Sodium Hydroxide → HCID 20495830, compound

HRID 1413793Notes

Reaction equation

HRID 1413793 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([OH:15])=[O:14])=[N:4][NH:3]1.[OH-].[Na+].[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>CO>[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:3]2[N:4]=[C:5]([CH2:12][C:13]([OH:15])=[O:14])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]2=[O:1])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 685274-Bromobenzyl bromideHCID 348621(4-Oxo-3,4-dihydrophthalazin-1-yl)acetic acid

Product 1

HCID 20495830HCID 20495830, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,2-Dihydro-1-oxophthalazin-4-ylacetic acid (2.0 g.) was added to a solution of sodium hydroxide (0.9 g.) in methanol (50 ml.). A clear solution was obtained on slight warming, which was treated with 4-bromobenzyl bromide (2.6 g.). The mixture was then heated under reflux for 3 hours and then evaporated. The residue was treated with water (60 ml.) and the solution obtained was extracted with ether (3×60 ml.). The aqueous phase was then acidified to pH 2 with concentrated hydrochloric acid and the acid mixture extracted with ethyl acetate (150 ml.). The extracts were washed with water (50 ml.), dried (MgSO4) and evaporated. The solid obtained was recrystallised from a 1:4 v/v mixture of ethyl acetate and petrol (60-80) to give 2-(4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetic acid (0.6 g.), m.p. 179°-181° C.

Workup

  1. customA clear solution was obtained on slight warming, which
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for 3 hours
  4. customevaporated
  5. additionThe residue was treated with water (60 ml.)
  6. customthe solution obtained
  7. extractionwas extracted with ether (3×60 ml.)
  8. extractionthe acid mixture extracted with ethyl acetate (150 ml.)
  9. washThe extracts were washed with water (50 ml.)
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe solid obtained
  13. customwas recrystallised from a 1:4 v/v mixture of ethyl acetate and petrol (60-80)

Sources & evidence

ORD record
ord-3f103f54c354496e8290cdd5787926c4
Source dataset
uspto-grants-1981_02
Patent number
US04251528

Reaction notes

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