Isopropanol → Sodium 2-(2-fluoro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate

HRID 1074558Notes

Reaction equation

HRID 1074558 reaction equation
C[O-].[Na+:3].[F:4][C:5]1[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:6]=1[CH2:7][N:8]1[N:17]=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:22].C(O)(C)C>CO>[F:4][C:5]1[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:6]=1[CH2:7][N:8]1[N:17]=[C:16]([CH2:18][C:19]([O-:21])=[O:20])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:22].[Na+:3]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 5278PonalrestatHCID 10942334Sodium Methoxide

Product 1

HCID 23717654Sodium 2-(2-fluoro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of sodium methoxide (25 ml. of a 1.0 M solution in methanol) was added to a solution of 2-(2-fluoro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid (9.87 g.) in methanol (300 ml.) and the mixture heated to its boling point. Methanol was then allowed to boil off until the volume of the mixture was approximately 100 ml. Isopropanol (150 ml.) was then added, followed by petrol (60-80) until the mixture was just opaque. The mixture was then allowed to cool to room temperature. The solid which formed was separated by filtration, evaporated with toluene (2×400 ml.) and then washed with ether (300 ml.) to give sodium 2-(2-fluoro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate, 6.5 g., m.p. 244°-247° C.

Workup

  1. temperaturethe mixture heated to its boling point
  2. customThe solid which formed
  3. customwas separated by filtration
  4. customevaporated with toluene (2×400 ml.)
  5. washwashed with ether (300 ml.)

Sources & evidence

ORD record
ord-b0dd3aee4653478ba08c691d4082d469
Source dataset
uspto-grants-1983_07
Patent number
US04393062

Reaction notes

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