Dimethylformamide → HCID 18415841, compound

HRID 990993Notes

Reaction equation

HRID 990993 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].CN(C)C=O>ClCCl>[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[O:19][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 9859735HCID 9859735, compound

Product 1

HCID 18415841HCID 18415841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(1,4-dihydroindeno-[1,2-c]pyrazol-3-yl)phenol (2.4 g), anhydrous potassium carbonate (1.2 g), ethyl 2-bromoacetate (1.2 ml) and dry dimethylformamide (20 ml) was stirred at ambient temperature for 24 hours. The mixture was diluted with dichloromethane (200 ml), washed with water, then 1N sodium hydroxide solution. The organic layer was separated, dried, filtered and evaporated to give an oil which was purified by flash column chromatography on silica using ethyl acetate/petroleum ether b.p. 60-80° C. (1:2 as the mobile phase). Appropriate fractions were combined and evaporated to give ethyl 3-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenoxyacetate, m.p. 134-136° C.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by flash column chromatography on silica
  8. customevaporated

Sources & evidence

ORD record
ord-c96540bc9893452f86a66187fe2aef31
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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