Sodium Hydroxide → HCID 54202380, compound

HRID 2082405Notes

Reaction equation

HRID 2082405 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[OH-].[Na+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>CN(C)C=O>[CH3:27][O:26][C:24]([CH2:23][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]=1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 60984Methyl bromoacetateHCID 7723355benzyl 1H-indole-2-carboxylate

Product 1

HCID 54202380HCID 54202380, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5 g of benzyl indole-2-carboxlate in solution in 20 ml of dimethylformamide are introduced slowly into 30 ml of a suspension of 1 g of NaOH in 30 ml of dimethylformamide and 3.1 g of methyl bromoacetate are then introduced. After 12 hours at ambient temperature, with stirring, the mixture is poured into a volume of ice-water and then extracted with ethyl acetate. The dried organic phase is concentrated and the residue is recrystallised from aqueous ethanol (95%, V/V). m.p.=94° C.; yield 87%.

Workup

  1. additionare then introduced
  2. extractionextracted with ethyl acetate
  3. concentrationThe dried organic phase is concentrated
  4. customthe residue is recrystallised from aqueous ethanol (95%, V/V)

Sources & evidence

ORD record
ord-3fef0288162b4f35a2e0f611b67d7e6d
Source dataset
uspto-grants-1993_02
Patent number
US05189049

Reaction notes

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