Water → HCID 15063405, compound

HRID 486765Notes

Reaction equation

HRID 486765 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:9]2=[CH:10][C:11]3[C:16]([N:8]2[CH2:7][CH2:6][C:5]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=[CH:13][CH:12]=3.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CN(C=O)C>[CH2:20]([O:19][C:17]([C:5]1([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:6][CH2:7][N:8]2[C:16]3[C:11]([CH:10]=[C:9]2[C:4]1=[O:3])=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 54678585HCID 54678585, compound

Product 1

HCID 15063405HCID 15063405, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.3 g of sodium hydride were added over 0.5 hour to a stirred, ice-cold solution of 12.85 g of ethyl 6,7-dihydro-9-hydroxypyrido[1,2-a]indole-8-carboxylate in 200 ml of DMF and the mixture was stirred for a further 0.5 hour. A solution of 9.2 g of ethyl bromoacetate in 50 ml of DMF was added dropwise to the cooled mixture. After a further 3 hours at room temperature the mixture was poured into 1.5 l of water and extracted with diethyl ether. The ethereal extracts were washed with water, dried and concentrated to give 16.3 g of ethyl 8-(ethoxycarbonyl)-6,7,8,9-tetrahydro-9-oxopyrido[1,2-a]indole-8-acetate.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ethereal extracts were washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fea3448e9b4842beaf252eb2806e5ad8
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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