Sodium Hydroxide → HCID 49787370, compound

HRID 420808Notes

Reaction equation

HRID 420808 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([O:20]CC)=[O:19])=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([OH:20])=[O:19])=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58986350HCID 58986350, compound2×

Product 1

HCID 49787370HCID 49787370, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

General Procedure E. A solution of ethyl 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylate (Compound 1, 1.1 g, 3.3 mmol) and NaOH (2.6 g, 65 mmol) in EtOH (20 ml) and H2O (10 ml) was heated to 100° C. for 16 h. The solvent was removed and the residue was treated with cold 6 M HCl (10.8 ml) and filtered. The resulting solid was washed with H2O (×3) and was taken in Et2O (∴3) to yield 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid (Compound 28) as a brown solid.

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with cold 6 M HCl (10.8 ml)
  3. filtrationfiltered
  4. washThe resulting solid was washed with H2O (×3)

Sources & evidence

ORD record
ord-3bd51f8813154bd280382f3416c17dd0
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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