Fusaric acid and analogous compounds. V. Syntheses of 3-alkylpicolinic acids and 5-methylpicolinic acid was written by Nakashima, Tatsumi. And the article was included in Yakugaku Zasshi in 1958.SDS of cas: 1122-71-0 This article mentions the following:
3,2-Me(H2N)C5H3N b6 86-8°; picrate, m. 226°. 2,3-BrMeC5H3N b6 67-9°. 3,2-Me(HO2C)C5H3N.H2O (I) m. 113°. A solution of 1.6 g. AgNO3 in 20% NH4OH, 1.6 g. NaOH, and 16 ml. H2O treated with 1 g. 3,2-Me(OHC)C5H3N, stirred 2 hrs., kept overnight, the solution filtered, the filtrate acidified with HCl, evaporated to dryness, the residue extracted with hot EtOH, the EtOH removed, the residue in H2O adjusted to pH 3-4, the solution treated with (AcO)2Cu, the Cu salt decomposed with H2S, the solution filtered, the filtrate evaporated to dryness, and the residue extracted with EtOH gave 0.2 g. I, m. 113° (petr. ether). MeC(:NH)CH2COR (R = Me) (16.3 g.) and 28.5 g. EtOCH:CHCH(OEt)2 heated 2 days at 100°, the product in 10% HCl extracted with Et2O, and distilled gave 12.5 g. 2,3-Me(RCO)C5H3N (II, R = Me), b15 102-3°; picrate, m. 171-3°. Similarly were prepared II (R, % yield, b.p/mm., and m.p. of picrate given): Et, 52.9, 108-10°/9, 145-7°; Pr, 73.4, 110-13°/8, 90-2°; Bu, 64.5, 123-6°/10, 93-4°. Wolff-Kishner reduction of II gave 2,3-Me(RCH2)C5H3N (III) (R, % yield, b.p./mm., and m.p. of picrate given): Me, 76.5, 63-4°/13, 139-40°; Et, 76.2, 80-1°/14, 129-30°; Pr, 66.7, 96-9°/14, 130-1°; Bu, 63.6, 95-105°/8, 97-8°. III converted to their N-oxides, refluxed 2 hrs. with Ac2O, and the product distilled gave 3,2-R(AcOCH2)C5H3N (IV) (R, % yield, b.p./mm., and m.p. of picrate given): Et, 66.9, 131-2°/13, 156-7°; Pr, 60.8, 135-6°/9, 146-7°; Bu, 78.2, 150-2°/11, 105-6°; Am, 74.1, 158-9°/9, -. IV in HCl refluxed 10 hrs., the product concentrated, the residue made alk. with K2CO3, and extracted with CHCl3 gave 3,2-R(HOCH2)C5H3N (V), (R, % yield, b.p./mm., and m.p. of picrate given): Et, 53.1, 112-14°/8, 131-2°; Pr, 62.9, 130-2°/8, 174-5°; Bu, 61.6, 135-7°/8, 153-4°; Am, 55.2, 140-4°/8, 126-7°. V (R = Et) (2.6 g.) and 26 g. MnO2 in Et2O heated 2.5 hrs. at 35° and the product distilled gave 1.6 g. 3,2-R(OHC)C5H3N (VI, R = Et), b8 68-70°; semicarbazone, m. 177° (decomposition). Similarly were prepared VI (R, % yield, b.p./mm., and m.p. of semicarbazone given): Pr, 59.9, 63-5°/9, 182-3°; Bu, 60.7, 95-102°/8, 200-1°; Am, 54.6, 100-4°/9, 96-7°. Oxidation of VI with Ag2O yielded 3,2-R(HO2C)C5H3N (VII) (R, % yield, and m.p. given): Et, 19.5, 72-3°; Pr, 18.2, 67-8°; Bu, 17.5, 55-7°; Am, 13.8, 71-2°. 6,3-Me(MeO2C)C5H3N (32 g.) added dropwise to 8.8 g. LiAlH4 in 500 ml. Et2O, refluxed 1 hr., the product poured in ice H2O, the aqueous layer treated with K2CO3, and the precipitate taken up in CHCl3 gave 15.1 g. 6,2-Me(HOCH2)C5H3N (VII), b8 130-2°, m. 46°. SOCl2 (100 ml.) at 0° treated portionwise with 15.1 g. VII, kept 30 min., refluxed 1 hr., the product conductivity in vacuo, the residue in ice H2O made alk. with K2CO3, and extracted with Et2O gave 6,3-Me(ClCH2)C5H3N; this in 100 ml. MeOH reduced with 50% Pd-C and H, the MeOH removed, the residue in H2O made alk. with Na2CO3, and extracted with Et2O gave 6 g. 2,5-Me2C5H3N (VII), b. 157-9°; picrate, m. 166-8°. VIII (6 g.) converted to its N-oxide and this and 6 ml. Ac2O refluxed 1 hr. gave 5 g. 5,2-Me(AcOCH2)C5H3N (IX), b15 124-4°; picrate, m. 130-1°. IX (5 g.) in 50 ml. HCl refluxed 10 hrs. gave 2.7 g. 5,2-Me(HOCH2)C5H3N (X), b8 94-7°; picrate, m. 168°. Oxidation of 2.7 g. X with MnO2 gave 1 g. 5,2-Me(OHC)C5H3N (XI), m. 35-6°. Oxidation of 1 g. XI with Ag2O gave 0.2 g. 5,2-Me(HO2C)C5H3N, m. 164-6°. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0SDS of cas: 1122-71-0).
6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.SDS of cas: 1122-71-0
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts