Trifluoroacetic acid → 7-(aminocarbonyl)-1H-indole-4-carboxylic acid

HRID 906117Notes

Reaction equation

HRID 906117 reaction equation
[C:1]([C:4]1[C:12]2[NH:11][CH:10]=[CH:9][C:8]=2[C:7]([C:13]([O:15]C(C)(C)C)=[O:14])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl>[NH2:2][C:1]([C:4]1[C:12]2[NH:11][CH:10]=[CH:9][C:8]=2[C:7]([C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67404011tert-butyl 7-carbamoyl-1H-indole-4-carboxylate

Product 1

HCID 577483337-(aminocarbonyl)-1H-indole-4-carboxylic acidYield 135.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4: To a solution of tert-butyl 7-carbamoyl-1H-indole-4-carboxylate (0.15 g, 0.58 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (10 mL), and the mixture was heated to reflux until the starting material was fully consumed. The solvent was evaporated followed by rotary evaporation of the residue from a mixture of ethyl acetate (50 mL) and toluene (50 mL). The procedure was repeated three times and the residue dried in vacuo to obtain 7-(aminocarbonyl)-1H-indole-4-carboxylic acid (0.16 g, 89%). MS (EI) for C10H8N2O3: 205 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux until the starting material
  3. customwas fully consumed
  4. customThe solvent was evaporated
  5. customfollowed by rotary evaporation of the residue from a mixture of ethyl acetate (50 mL) and toluene (50 mL)
  6. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-c0f20ce342dc47d8a2a5124a0174d299
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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