Acetanilide → HCID 24821527, compound

HRID 1028392Notes

Reaction equation

Br[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[C:13]1([NH:19][C:20](=O)[CH3:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:12][O:11][C:4]1[N:3]=[C:2]2[N:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:20]([CH3:21])=[N:8][C:7]2=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 904Acetanilide

HCID 130403842-Bromo-6-methoxy-3-nitropyridine

Product 1

HCID 24821527HCID 24821527, compoundYield 94%

Procedure

The title compound was prepared with the analogous procedure described in example 3 using 2-Bromo-6-methoxy-3-nitropyridine (116 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) as starting materials to yield the title compound as pale yellow solid (112 mg, 94%). mp 114-116° C. 1H NMR (DMSO) δ 2.56 (s, 3 H), 3.76 (s, 3 H), 6.85 (d, J=8.6 Hz, 1 H), 7.53-7.68 (m, 5 H), 8.12 (d, J=8.6 Hz, 1 H). 13C NMR δ 13.8, 53.4, 107.7, 122.9, 127.0, 128.0, 128.4, 129.2, 132.6, 144.1, 150.3, 161.1. HRMS (FAB): cal. for C14H14N3O [M-FH+]: 240.1237; found: 240.1234.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-b8ec3a0e66d74cf5b5406279c9518b4e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

Loading…