Ethyl 2-(2-cyanoanilino)acetate → Ethyl 3-amino-1H-indole-2-carboxylate

HRID 1728405Notes

Reaction equation

HRID 1728405 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]#[N:14])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1.[Cl-].[NH4+]>[NH2:14][C:13]1[C:8]2[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:6][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:15]

Participants

5

Reactant 2

HCID 2779716Ethyl 2-(2-cyanoanilino)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 732887Ethyl 3-amino-1H-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of N-(2-Cyanophenyl)glycine ethyl ester (8.1 g) in THF (125 mL) was added potassium t-butoxide (4.5 g) in one portion with stirring. After 10 min at room temperature the mixture was diluted with saturated ammonium chloride solution and the product was extracted with ether. After drying over magnesium sulfate the solvent was removed in vacuo and the residue was recrystallized from 80% methanol to afford 3-Amino-2-carboethoxyindole as a tan solid.

Workup

  1. extractionthe product was extracted with ether
  2. dry with materialAfter drying over magnesium sulfate the solvent
  3. customwas removed in vacuo
  4. customthe residue was recrystallized from 80% methanol

Sources & evidence

ORD record
ord-257f685040c44c758c0bae71dde27b76
Source dataset
uspto-grants-1994_07
Patent number
US05326868

Reaction notes

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