Acetanilide → HCID 24821529, compound

HRID 1931282Notes

Reaction equation

HRID 1931282 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[CH:5]=[CH:4][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][CH:4]=[CH:5][C:6]([CH3:11])=[C:7]2[N:8]=1

Participants

3

Reactant 2

HCID 904AcetanilideHCID 3453632-Chloro-4-methyl-3-nitropyridine

Product 1

HCID 24821529HCID 24821529, compoundYield 63%

Procedure

Method A applied to 2-chloro-4-methyl-3-nitropyridine (86 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) afforded the title compound as pale yellow solid (70 mg, 63%). mp 117-119° C. 1H NMR (DMSO) δ 2.59 (s, 3H), 2.73 (s, 3H), 7.26 (d, J=4.8Hz, 1H), 7.58-7.72 (m, 5H), 8.22 (d, J=4.8Hz, 1H); 13C NMR δ 13.8, 16.0, 120.8, 127.3, 129.3, 129.4, 129.5, 130.1, 136.0, 144.2, 146.4, 152.1. HRMS (FAB): cal. for C14H14N3 [M+H+]: 224.1188; found: 224.1180.

Sources & evidence

ORD record
ord-85108ad5256449aa9d44917dbbc3fc04
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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