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

HRID 2293222Notes

Reaction equation

HRID 2293222 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-d42609a7b4e748ff8198df481772fd70
Source dataset
uspto-grants-1997_11
Patent number
US05686445

Reaction notes

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