Ethanol → ethyl 3-amino-5-chloro-1H-indole-2-carboxylate

HRID 1376103Notes

Reaction equation

HRID 1376103 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7](C(=O)C(F)(F)F)[C:8]2[C:13]([C:14]=1[NH2:15])=[CH:12][C:11]([Cl:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(O)C.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:16])[CH:12]=2)[NH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium Carbonate2×HCID 69009594HCID 69009594, compound

Product 1

HCID 3614734ethyl 3-amino-5-chloro-1H-indole-2-carboxylateYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Heat at 70° C. and stir a mixture of 3-amino-5-chloro-1-(2,2,2-trifluoro-ethanoyl)-1H-indole-2-carboxylic acid ethyl ester (3.34 g, 10 mmol), ethanol (50 mL), and potassium carbonate (1.50 g, 10.85 mmol). After 1.75 h, add water (20 mL), and after another hour add additional potassium carbonate (0.58 g, 4.20 mmol). Cool the reaction mixture to ambient temperature and partition between water/ethyl acetate. Separate the organic layer, dry over MgSO4, filter and concentrate to afford 1.70 g of the title compound as a solid. MS 239(M+H).

Workup

  1. temperatureCool the reaction mixture to ambient temperature
  2. custompartition between water/ethyl acetate
  3. customSeparate the organic layer
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-70c86cf464e0480c902472fba6acb36b
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

Loading…