Ammonia → N-tert-Butyl-3-methylpyridine-2-carboxamide

HRID 1606943Notes

Reaction equation

[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].S(=O)(=O)(O)[OH:11].N.[C:16](O)([CH3:19])([CH3:18])[CH3:17]>O.C1(C)C=CC=CC=1>[CH3:17][C:16]([NH:2][C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:11])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 2-cyano-3-methyl pyridine (400 g; 3.4 mol) in 800 mL of t-butanol was heated at 70° C. Concentrated sulfuric acid (400 mL) was added over 45 min. The reaction was complete after a further 30 min. at 75° C. The reaction mixture was diluted with water (400 mL) and toluene (600 mL) and brought to pH 10 with concentrated aqueous ammonia. The temperature was kept at 50°-55° C. during work-up. The toluene phase was separated, the aqueous layer extracted again with toluene and the combined toluene phases were washed with water. Removal of the toluene yielded 633 g (97%) of crystalline N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide: m.p. 56°-58° C.; NMR 9200 MHz, CDCl3)δ1.52 (s,9H); 2.75 (s,3H); 7.25 (dd,1H, J=7.5, 5 Hz); 7.58 (dd,1H, J=7.5, 1.2 Hz); 8.08 (br s, 1H); 8.40 (dd,1H, J=5), 1.2 Hz); mass spectrum, m/e (rel intensity) 192M+ (12), 177 (49). Anal. Calcd for C11H16N2O: C,68.68; H, 8.13; N,14.40. Found: C,68.71; H,8.39; N,14.57.

Workup

customwas kept at 50°-55° C. during work-up
customThe toluene phase was separated
extractionthe aqueous layer extracted again with toluene
washthe combined toluene phases were washed with water
customRemoval of the toluene

Sources & evidence

ORD record: ord-62197d55981448e59b2fc3338e8e727c
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863931

Reaction notes

Loading…