Ethanol → 3-Amino-6-chloro-2-(3-methylbenzoyl)-1H-indole

HRID 651010

Reaction equation

HRID 651010 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4](C(OCC)=O)[C:3]=1[C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=1.C([O-])([O-])=O.[K+].[K+].CCO>O>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 183680433-Amino-6-chloro-2-(3-methylbenzoyl)-1-(ethoxycarbonyl)indole

Product 1

HCID 183678773-Amino-6-chloro-2-(3-methylbenzoyl)-1H-indoleYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-amino-6-chloro2-(3-methylbenzoyl)-1H-indole-1-caboxylate (step 1, 6.4 g, 18 mmol), K2CO3 (6.3 g, 45 mnmol) , EtOH (50 ml) and water (30 ml) was heated at reflux temperature for 20 h. The mixture was concentrated, and then water (30 ml) was added to the residue. The resulting mixture was extracted with dichloromethane (80 ml×2) and the combined extracts were dried (MgSO4). Removal of solvent gave 4.3 g (84%) of brown amorphous solids.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 20 h
  3. concentrationThe mixture was concentrated
  4. additionwater (30 ml) was added to the residue
  5. extractionThe resulting mixture was extracted with dichloromethane (80 ml×2)
  6. dry with materialthe combined extracts were dried (MgSO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-78ad45ccc9a54c70a1c8741eceb8479b
Source dataset
uspto-grants-2001_08
Patent number
US06277878B1

Linked notes

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