Acetanilide → HCID 24821526, compound

HRID 1931279Notes

Reaction equation

HRID 1931279 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH3:11])=[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]=[C:5]([CH3:11])[CH:6]=[C:7]2[N:8]=1

Participants

3

Reactant 2

HCID 904AcetanilideHCID 8183002-Chloro-5-methyl-3-nitropyridine

Product 1

HCID 24821526HCID 24821526, compoundYield 81%

Procedure

Method A applied to 2-chloro-5-methyl-3-nitropyridine (86 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) afforded the title compound as brown solid (90 mg, 81%). mp 77-79° C. 1H NMR (DMSO) δ 2.44 (s, 3H), 2.54 (s, 3H), 7.56-7.63 (m, 5H), 7.95 (s, 1H), 8.20 (s, 1H); 13C NMR δ 13.1, 17.9, 124.4, 127.5, 129.5, 129.6, 129.8, 132.9, 145.1, 145.7, 153.2. HRMS (FAB): cal. for C14H14N3 [M+H+]: 224.1187; found: 224.1184.

Sources & evidence

ORD record
ord-6525afe8ef9342c3bececd48dee271dc
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

Loading…