Acetanilide → HCID 24821528, compound

HRID 1931281Notes

Reaction equation

HRID 1931281 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.[C:12]1([NH:18][C:19](=O)[CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:20][C:19]1[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]2=[N:3][C:4]([CH3:11])=[CH:5][CH:6]=[C:7]2[N:8]=1

Participants

3

Reactant 2

HCID 904AcetanilideHCID 12682302-Chloro-6-methyl-3-nitropyridine

Product 1

HCID 24821528HCID 24821528, compoundYield 63%

Procedure

Method A applied to 2-chloro-6-methyl-3-nitropyridine (86 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) afforded the title compound as brown viscous oil (70 mg, 63%). 1H NMR (DMSO) δ 2.42 (s, 3H), 3.31 (s, 3H), 7.11 (d, J=8.0Hz, 1H), 7.51-7.63 (m, 5H), 7.89 (d, J=8.0Hz, 1H); 13C NMR δ 14.6, 23.8, 118.0, 126.1, 127.7, 128.7, 129.4, 132.1, 134.8, 148.3, 150.9, 151.1. HRMS: cal. for C14H14N3 [M+H+]: 224.1188; found: 224.1184.

Sources & evidence

ORD record
ord-877fe083b71c4a369439b141bd4da4fc
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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