Water → 4-bromo-1-(4-nitrobenzoyl)-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

HRID 1288951Notes

Reaction equation

HRID 1288951 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14](=[O:21])[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:24]Br.O>C(O)(=O)C>[Br:24][CH:13]1[C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:10]([C:8](=[O:9])[C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:23][CH:22]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 107337295H-1-Benzazepin-5-one, 1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-

Product 1

HCID 540926514-bromo-1-(4-nitrobenzoyl)-3,4-dihydro-1H-benzo[b]azepin-5(2H)-oneYield 87.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 0.200 g of 1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepin-5-one in 2.5 ml of acetic acid is warmed until solution then allowed to cool to room temperature. While stirring, a solution of 0.103 g of bromine in 0.5 ml of acetic acid is added dropwise. After rapid decolorization, the reaction mixture is stirred for 1.5 hours and poured into water. The solid is collected, washed with water and air dried to give 220 mg of the desired product as a crystalline solid, Mass Spectrum; MH+ =389,391.

Workup

  1. temperatureis warmed until solution
  2. stirringAfter rapid decolorization, the reaction mixture is stirred for 1.5 hours
  3. customThe solid is collected
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-9a935996135545f088ec4db01d2cb5fa
Source dataset
uspto-grants-1998_05
Patent number
US05747487

Reaction notes

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