Water → HCID 20495853, compound

HRID 1413801Notes

Reaction equation

HRID 1413801 reaction equation
C(=O)([O-])[O-].[K+].[K+].O.[F:8][C:9]1[CH:33]=[C:32]([Br:34])[CH:31]=[CH:30][C:10]=1[CH2:11][N:12]1[N:21]=[C:20]([CH2:22][C:23]([O:25]CC)=[O:24])[C:19]2[C:14](=[C:15]([F:28])[CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:29]>O1CCOCC1>[F:8][C:9]1[CH:33]=[C:32]([Br:34])[CH:31]=[CH:30][C:10]=1[CH2:11][N:12]1[N:21]=[C:20]([CH2:22][C:23]([OH:25])=[O:24])[C:19]2[C:14](=[C:15]([F:28])[CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:29]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 20495822HCID 20495822, compound

Product 1

HCID 20495853HCID 20495853, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of potassium carbonate (1.5 g.), water (16 ml.), dioxan (50 ml.) and ethyl 2-(2-fluoro-4-bromobenzyl)-8-fluoro-1,2-dihydro-1-oxophthalazin-4-ylacetate (1.0 g.) was heated under reflux for 24 hours, and then evaporated. The residue was dissolved in water (100 ml.) and the solution washed with ether (2×100 ml.). The aqueous phase was acidified to pH 2 by addition of concentrated hydrochloric acid. The solid which formed was collected by filtration, washed with water, and recrystallised from a 7:1:5 v/v/v mixture of toluene/isopropanol/petrol (60-80) to give 2-(2-fluoro-4-bromobenzyl)-8-fluoro-1,2-dihydro-1-oxophthalazin-4-ylacetic acid (Example 36) (0.5 g.), m.p. 173°-175° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customevaporated
  4. dissolutionThe residue was dissolved in water (100 ml.)
  5. washthe solution washed with ether (2×100 ml.)
  6. additionThe aqueous phase was acidified to pH 2 by addition of concentrated hydrochloric acid
  7. customThe solid which formed
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customrecrystallised from a 7:1:5 v/v/v mixture of toluene/isopropanol/petrol (60-80)

Sources & evidence

ORD record
ord-2623cccd0284403d8f4d46dd8a9ca633
Source dataset
uspto-grants-1981_02
Patent number
US04251528

Reaction notes

Loading…