Hydrochloric Acid → HCID 117779496, compound

HRID 1527027Notes

Reaction equation

HRID 1527027 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([O:21]CC)=[O:20])=[C:11]2C)[CH3:9])=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([OH:21])=[O:20])=[CH:11]2)[CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 117778937HCID 117778937, compound

Product 1

HCID 117779496HCID 117779496, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a mixture of ethyl 1-(1-(4-chlorophenyl)ethyl)-2-methyl-1H-indole-3-carboxylate (210 mg, 0.61 mmol) in MeOH/H2O (6 mL/2 mL) was added KOH (340 mg, 6.1 mmol) at room temperature. The reaction was refluxed overnight. Then the mixture was adjusted to Ph=4 with 1 N HCl and extracted with EtOAc (3×). The combined organic extract were combined and concentrated in vacuo to afford the title compound as a yellow solid (200 mg, yield 105%) which was used without further purification.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. extractionextracted with EtOAc (3×)
  3. extractionThe combined organic extract
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90b027e2af8b48f89da90bb8471256a0
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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