Acetanilide → HCID 12239330, compound

HRID 1931276Notes

Reaction equation

HRID 1931276 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[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[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N:8]=1

Participants

3

Reactant 2

HCID 904AcetanilideHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 12239330HCID 12239330, compoundYield 72.6%

Procedure

Method A applied to 4-chloro-3-nitropyridine (79 mg, 0.5 mmol), N-phenylacetamide (81 mg, 0.6 mmol) afforded the title compound as brown solid (76 mg, 73). mp 134-136° C. 1H NMR (DMSO) δ 2.54 (s, 3H), 7.65-7.73 (m, 6H), 8.54 (d, J=5.2Hz, 1H), 9.44 (s, 1H); 13C NMR δ 14.4, 108.2, 126.9, 130.2, 130.3, 133.4, 134.0, 134.8, 139.2, 145.0, 159.2. HRMS (FAB): cal. for C13H12N3 [M+H+]: 210.1031; found: 210.1025.

Sources & evidence

ORD record
ord-77ad3ec9fc394c3ea3a0eee9db9e83a3
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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