Citric Acid → 2-Carbomethoxy-3-indolylacetonitrile

HRID 1111379Notes

Reaction equation

HRID 1111379 reaction equation
CN([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:14]([O:16][CH3:17])=[O:15])C.C(Br)C.[C-:21]#[N:22].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[CH3:17][O:16][C:14]([C:6]1[NH:7][C:8]2[C:13]([C:5]=1[CH2:4][C:21]#[N:22])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:15]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6332Ethyl BromideHCID 9032Potassium CyanideHCID 109114233-Dimethylaminomethyl-2-methoxycarbonylindole

Product 1

HCID 126444222-Carbomethoxy-3-indolylacetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

40.6 g Product from (b) were dissolved in 300 ml DMSO and 14.5 ml ethylbromide were added. After 10 minutes, 11.4 g KCN were added and the mixture was stirred for 48 hours. The reaction mixture was poured into citric acid and extracted with CH2Cl2. The solvent was evaporated to give 26 g yellow residue.

Workup

  1. extractionextracted with CH2Cl2
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9083242bed2143cebeecf2b64877daae
Source dataset
uspto-grants-1990_12
Patent number
US04980368

Reaction notes

Loading…