Ethanol → HCID 11652052, compound

HRID 1376107Notes

Reaction equation

HRID 1376107 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7](C(=O)C)[C:8]2[C:13]([C:14]=1[NH2:15])=[CH:12][CH:11]=[C:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:9]=2)=[O:5])[CH3:2].C(O)C>O>[NH2:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 702EthanolHCID 69010457HCID 69010457, compound

Product 1

HCID 11652052HCID 11652052, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Reflux a mixture of 3-amino-1-(ethanoyl)-6-phenyl-1H-indole-2-carboxylic acid ethyl ester (7.3 g, 22.6 mmol) 20% aqueous potassium carbonate (100 mL) and ethanol (100 mL) for 1.75 h. Let the reaction stand at ambient temperature overnight and dilute with water (500 mL). Cool at 0° C. and collect a purple solid. Wash the solid with water and dry at 40° C. under vacuum and obtain 5.7 g of a purple solid. Triturate the solid with dichloromethane (40 mL) filter and wash the solid with dichloromethane and ethyl acetate, and then dry at 40° C. under vacuum to obtain 2.5 g of the title compound as a solid:

Workup

  1. temperatureReflux
  2. customat ambient temperature
  3. customovernight
  4. customcollect a purple solid
  5. washWash the solid with water
  6. customdry at 40° C. under vacuum

Sources & evidence

ORD record
ord-16a0497e95b146e9b83f52fff6ced7af
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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