Acetanilide → HCID 24821451, compound

HRID 1931277Notes

Reaction equation

HRID 1931277 reaction equation
Cl[C:2]1[C:3]([N+:8]([O-])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:11]1([NH:17][C:18](=O)[CH3:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:19][C:18]1[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]2[C:3]([N:8]=1)=[N:4][CH:5]=[CH:6][CH:7]=2

Participants

3

Reactant 2

HCID 904AcetanilideHCID 5549883-Chloro-2-nitropyridine

Product 1

HCID 24821451HCID 24821451, compoundYield 43.2%

Procedure

Method A applied to 3-chloro-2-nitropyridine (79 mg) and N-phenylacetamide (81 mg, 0.6 mmol) afforded the title compound as brown viscous oil (45 mg, 43% yield). 1H NMR (DMSO) δ 2.54 (s, 3H), 7.35-7.68 (m, 6H), 7.77 (d, J=8.8Hz, 1H), 8.58 (br s, 1H); 13C NMR δ 14.0, 118.9, 120.1, 126.8, 128.5, 129.6, 130.1, 133.9, 143.0, 151.6, 156.7. HRMS (FAB): cal. for C13H12N3 [M+H+]: 210.1031; found: 210.1026.

Sources & evidence

ORD record
ord-5b32159c36314340b462c4bfdb093e17
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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