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

HRID 1413799
Notes
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Reaction equation

HRID 1413799 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-c263b125d14a4394ac270b1b12239bcf
Source dataset
uspto-grants-1981_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04251528

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes