Ethyl chloroacetate → Carbethoxymethyl beta-carbolin-3-carboxylate

HRID 1757963Notes

Reaction equation

HRID 1757963 reaction equation
[H-].[Na+].[CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]([C:16]([OH:18])=[O:17])[N:4]=1.Cl[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C)C=O>[CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]([C:16]([O:18][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[N:4]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 20059983Carbethoxymethyl beta-carbolin-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.4 g of a 55% suspension of sodium hydride in mineral oil are added to a suspension of 2.1 g of β-carbolin-3-carboxylic acid in 25 ml of dimethyl formamide, and after a period of 5 minutes, 1.2 ml of ethyl chloracetate are added. The mixture is refluxed for 4 hours and subsequently dimethyl formamide is evaporated in vacuo. After addition of 100 ml of water to the remainder, the mixture is extracted with chloroform to form 1 g of carbethoxymethyl β-carbolin-3-carboxylate having a melting point of 202°-203° C.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. customsubsequently dimethyl formamide is evaporated in vacuo
  3. additionAfter addition of 100 ml of water to the remainder
  4. extractionthe mixture is extracted with chloroform

Sources & evidence

ORD record
ord-159e246cbeac4f5eb765bc3608bb5fff
Source dataset
uspto-grants-1983_02
Patent number
US04371536

Reaction notes

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