4-Methyl-3-nitroaniline → HCID 22057993, compound

HRID 1357694Notes

Reaction equation

C(N(CC)CC)C.[N+:8]([C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[CH3:18])[NH2:14])([O-:10])=[O:9].[C:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)#[N:20]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:18][C:17]1[CH:16]=[CH:15][C:13]([NH:14][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([C:19]#[N:20])=[CH:22][CH:23]=2)=[CH:12][C:11]=1[N+:8]([O-:10])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (23 ml) was added to a suspension of 3-nitro-4-methylaniline (0.8 g), 4-cyanobenzoyl chloride (13.1 g), 4-dimethylaminopyridine (0.8 g) in methylene chloride (200 ml) which had been cooled to 0° C. The reaction mixture was allowed to warm to ambient temperature and was stirred for 5 hours. The mixture was partitioned between methylene chloride and 0.5M hydrochloric acid solution. The organic phase was dried over magnesium sulphate, filtered and evaporated to dryness. The residue was triturated under isohexane and the resulting solid was isolated and dried under vacuum at 55° C. to yield N-(4-methyl-3-nitrophenyl)-4-cyanobenzamide (18.3 g); NMR: 2.5 (s, 3H), 7.49 (d, 1H), 7.96 (m, 1H), 8.05 (d, 2H), 8.12 (d, 2H), 8.51 (d, 1H), 10.77 (s, 1H).

Workup

temperatureto warm to ambient temperature
customThe mixture was partitioned between methylene chloride and 0.5M hydrochloric acid solution
dry with materialThe organic phase was dried over magnesium sulphate
filtrationfiltered
customevaporated to dryness
customThe residue was triturated under isohexane
customthe resulting solid was isolated
customdried under vacuum at 55° C.

Sources & evidence

ORD record: ord-ff2742aec4104cf5bf0ef7f49bf96bbe
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06593333B1

Reaction notes

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