Water → Ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate

HRID 1074549Notes

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]([O:15][CH2:16][CH3:17])=[O:14])=[N:4][NH:3]1.[H-].[Na+].[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][C:22]=1[Cl:29].O>CN(C)C=O>[Cl:29][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:21]=1[Br:20])[CH2:25][N:3]1[N:4]=[C:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]1=[O:1]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 1,2-dihydro-1-oxophthalazin-4-ylacetate (11.5 g.) and sodium hydride (2.7 g.; 50% w/w dispersion in mineral oil) in dimethylformamide (125 ml.) was stirred at 60° C. for 1 hour under nitrogen. The solution obtained was cooled to room temperature and then 4-bromo-3-chlorobenzyl bromide (15.0 g.) was added, and the mixture stirred at 60° C. for 2 hours. After cooling to 25° C. the reaction mixture was poured into water (500 ml.). The aqueous mixture obtained was extracted with ethyl acetate (400 ml.). The extracts were washed with water, dried (MgSO4), and evaporated to give a solid, which was crystallised from propan-2-ol to yield ethyl 2-(3-chloro-4-bromobenzyl)-1,2-dihydro-1-oxophthalazin-4-ylacetate (7.3 g.), m.p. 142°-145° C.

Workup

customThe solution obtained
temperaturewas cooled to room temperature
stirringthe mixture stirred at 60° C. for 2 hours
temperatureAfter cooling to 25° C. the reaction mixture
customThe aqueous mixture obtained
extractionwas extracted with ethyl acetate (400 ml.)
washThe extracts were washed with water
dry with materialdried (MgSO4)
customevaporated
customto give a solid, which
customwas crystallised from propan-2-ol

Sources & evidence

ORD record: ord-1bee9c7e61074308af24011cd4849793
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04393062

Reaction notes

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