Ethyl 2-(4-oxo-3,4-dihydrophthalazin-1-yl)acetate → 3,4-Dihydro-3-[2-[2-bromo-5-trifluoromethylphenylamino]-2-oxoethyl]-4-oxophthalazine-1-acetic acid ethyl ester

HRID 1464257Notes

Reaction equation

HRID 1464257 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.CC(C)([O-])C.[K+].[Br:24][C:25]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:26]=1[NH:27][C:28](=[O:31])[CH2:29]Cl>CN(C)C=O>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2](=[O:1])[N:3]([CH2:29][C:28]([NH:27][C:26]2[CH:32]=[C:33]([C:36]([F:37])([F:38])[F:39])[CH:34]=[CH:35][C:25]=2[Br:24])=[O:31])[N:4]=1)[CH3:17]

Participants

5

Reactant 3

HCID 348622Ethyl 2-(4-oxo-3,4-dihydrophthalazin-1-yl)acetateHCID 157139482'-Bromo-5'-trifluoromethyl-2-chloroacetanilideHCID 23665647Potassium tert-butoxide

Product 1

HCID 99580483,4-Dihydro-3-[2-[2-bromo-5-trifluoromethylphenylamino]-2-oxoethyl]-4-oxophthalazine-1-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 4-oxo-3H-phthalazin-1-ylacetate (3.36 g) and potassium t-butoxide (1.62 g) in dimethylformamide (15 ml) was slowly added a solution of 2'-bromo-5'-trifluoromethyl-2-chloroacetanilide (4.55 g) in dimethylformamide (15). After stirring the resulting solution overnight at room temperature, it was poured onto water (50 ml) and the resulting white precipitate was collected and air dried (yield 4.3 g; m.p. 160° C.).

Workup

  1. additionit was poured onto water (50 ml)
  2. customthe resulting white precipitate was collected
  3. customair dried (yield 4.3 g; m.p. 160° C.)

Sources & evidence

ORD record
ord-e6d0364450094fb992d558318d3066b3
Source dataset
uspto-grants-1994_04
Patent number
US05304557

Reaction notes

Loading…