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

HRID 1074554
Notes
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Reaction equation

HRID 1074554 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Br:11])[CH2:5][NH:6][NH2:7].[C:12](=[O:15])([O-])[OH:13].[Na+].[O:17]1[CH2:22][CH2:21]OCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Br:11])[CH2:5][N:6]1[N:7]=[C:9]([CH2:8][C:12]([OH:13])=[O:15])[C:10]2[C:21](=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:22]1=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 20495799[(4-Bromo-3-chlorophenyl)methyl]hydrazine

Product 1

HCID 204958292-(3-Chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-Chloro-4-bromobenzylhydrazine (2.5 g.) was added to a stirred mixture of 3-oxo-Δ1,α-phthalanacetic acid (also known as phthalideneacetic acid (1.92 g.) and sodium hydrogen carbonate (2.0 g.) in dioxan (50 ml.) and water (25 ml.). The mixture was then heated under reflux for 3 hours, cooled to room temperature and poured into water (200 ml.). The aqueous solution was extracted with ether (3×100 ml.) and the aqueous phase was acidified with concentrated hydrochloric acid to pH 2. The solid which deposited was collected, washed well with water, dried in vacuo, and then recrystallised twice from a mixture of toluene isopropanol and petrol (60-80) (6:2:3 v/v/v) to give 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid (0.23 g.), m.p. 184°-186° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 3 hours
  3. extractionThe aqueous solution was extracted with ether (3×100 ml.)
  4. customThe solid which deposited was collected
  5. washwashed well with water
  6. customdried in vacuo
  7. customrecrystallised twice from a mixture of toluene isopropanol and petrol (60-80) (6:2:3 v/v/v)

Sources & evidence

ORD record
ord-ed0024e3187c40f696a5c640eeae2b7a
Source dataset
uspto-grants-1983_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04393062

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes