Bromine → HCID 13712336, compound

HRID 2231210Notes

Reaction equation

HRID 2231210 reaction equation
BrBr.[Cl:3][C:4]1[CH:24]=[CH:23][C:7]2[CH2:8][CH2:9][CH:10]3[C:15]([C:6]=2[CH:5]=1)=[N:14][N:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:12](=[O:22])[CH2:11]3>C(O)(=O)C>[Cl:3][C:4]1[CH:24]=[CH:23][C:7]2[CH2:8][CH2:9][C:10]3[C:15]([C:6]=2[CH:5]=1)=[N:14][N:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:12](=[O:22])[CH:11]=3

Participants

4

Reactant 2

HCID 24408BromineHCID 13712335HCID 13712335, compound

Product 1

HCID 13712336HCID 13712336, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

About half volume of 10 ml of solution of 3.9 g of bromine in acetic acid is added dropwise to a solution of 5 g of 9-chloro-2-phenyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one in 150 ml of acetic acid with stirring at room temperature. After the mixture is heated up to 50° C. on a water bath, the remaining solution is added dropwise. After stirring under heating at 50° C. for 2 hours, the precipitated crystals are collected by filtration, washed with water and recrystallized from ethanol to give 2.7 g of 9-chloro-2-phenyl-5,6-dihydrobenzo[h]cinnolin-3(2H)-one as yellow leaflets, melting at 184°-186° C.

Workup

  1. temperatureAfter the mixture is heated up to 50° C. on a water bath
  2. additionthe remaining solution is added dropwise
  3. stirringAfter stirring
  4. temperatureunder heating at 50° C. for 2 hours
  5. filtrationthe precipitated crystals are collected by filtration
  6. washwashed with water
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0b83b7459451448c849e08985d767c08
Source dataset
uspto-grants-1988_11
Patent number
US04782057

Reaction notes

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