p-Anisoyl chloride → HCID 66894620, compound

HRID 252818Notes

Reaction equation

HRID 252818 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=2)=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[H-].[Na+].[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>N1C=CC=CC=1.CN(C=O)C>[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:16]=2)=[CH:7][C:5]=1[NH:6][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[CH:26][CH:27]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 24758Sodium hydrideHCID 59736969HCID 59736969, compound

Product 1

HCID 66894620HCID 66894620, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 102 (599 mg, 2.20 mmol), NaH 60% (141 mg, 3.52 mmol) and 4-methoxybenzoyl chloride (450 mg, 2.64 mmol) in pyridine (5 ml) and DMF (12 ml) was stirred at room temperature during 48 h. The solid was filtered out and rinsed with MeOH to give 584 mg (82%) of the title compound 103 as a yellow solid. 1H NMR: (400 MHz, DMSO) δ (ppm): 10.72 (s, 1H), 8.13-8.08 (m, 3H), 7.96 (d, J=8.8 Hz, 2H), 7.90 (d, J=8.6 Hz, 2H), 7.74 (dd, J=8.6, 2.2 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 3.89 (s, 3H), 3.86 (s, 3H).

Workup

  1. filtrationThe solid was filtered out
  2. washrinsed with MeOH

Sources & evidence

ORD record
ord-3fbc43a1524f422fbd68348445e4f2f7
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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