4-Nitrobenzoyl chloride → HCID 22405129, compound

HRID 441226Notes

Reaction equation

HRID 441226 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[C:7](=[O:16])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:5]=2[CH:4]=1.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]>CN(C)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[C:7](=[O:16])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[N:10]([C:26](=[O:27])[C:25]3[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=3)[CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 2846628-methoxy-5,6-dihydro-11h-dibenzo[b,e]azepin-11-one

Product 1

HCID 22405129HCID 22405129, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-methoxy-11-oxo-6,11- dihydrodibenz[b,e]azepine (150 mg) in N,N-dimethylaniline (1 ml) was added 4-nitrobenzoyl chloride (140 mg) at 110° C. The mixture was stirred for 1 hour at the same temperature and diluted with ethyl acetate. The solution was washed successively with diluted hydrochloric acid and brine. The organic phase was dried over magnesium sulfate, and evaporated in vacuo to give crude 8-methoxy -5-(4-nitrobenzoyl)-11-oxo-6,11-dihydrodibenz[b,e]azepine (240 mg).

Workup

  1. washThe solution was washed successively with diluted hydrochloric acid and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c56da12d13884577857b8a549bdd5e07
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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