Acetanilide → HCID 24821451, compound

HRID 1028390Notes

Reaction equation

HRID 1028390 reaction equation
Br[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 5940443-Bromo-2-nitropyridine

Product 1

HCID 24821451HCID 24821451, compoundYield 47%

Procedure

The title compound was prepared with the analogous procedure described in example 3 using 3-Bromo-2-nitropyridine (101 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) as starting materials to yield the title compound as brown viscous oil (49 mg, 47% yield). 1H NMR (DMSO) δ 2.54 (s, 3 H), 7.35-7.68 (m, 6 H), 7.77 (d, J=8.8 Hz, 1 H), 8.58 (br s, 1 H); 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-FH+]: 210.1031; found: 210.1026.

Workup

  1. customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record
ord-31b09b37a8c14224bf3abe50b5174384
Source dataset
uspto-grants-2014_05
Patent number
US08735586B2

Reaction notes

Loading…