Water → 2-(3-Chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid

HRID 1074550Notes

Reaction equation

HRID 1074550 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Br:26])[CH2:5][N:6]1[N:15]=[C:14]([CH2:16][C:17]([O:19]CC)=[O:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:22].[OH-].[K+].O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Br:26])[CH2:5][N:6]1[N:15]=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 20495807Ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate

Product 1

HCID 204958292-(3-Chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acidYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate (7.0 g.) in ethanol (70 ml.) containing potassium hydroxide (7.0 g.) was heated under reflux for 30 minutes. The solution was then poured into water (250 ml.) and the aqueous solution was extracted with ether (2×150 ml.). The aqueous phase was acidified to pH 2 with concentrated hydrochloric acid. The solid which was thus precipitated was separated, washed with water, dried in vacuo and then recrystallised from a 6:2:3 v/v mixture of toluene, propan-2-ol and petrol (60-80) to give 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid (3.9 g.), m.p. 186° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. extractionthe aqueous solution was extracted with ether (2×150 ml.)
  4. customThe solid which was thus precipitated
  5. customwas separated
  6. washwashed with water
  7. customdried in vacuo
  8. customrecrystallised from a 6:2:3 v/v mixture of toluene, propan-2-ol and petrol (60-80)

Sources & evidence

ORD record
ord-2a9ff9fc668642d0b3f94f0e97c2f8d6
Source dataset
uspto-grants-1983_07
Patent number
US04393062

Reaction notes

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