Methanol → 6-Hydroxy-a-methyl carbazole-2-acetic acid

HRID 484260Notes

Reaction equation

HRID 484260 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([CH3:20])[C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=3)[NH:9][C:8]=2[CH:7]=1)C.[OH-].[K+].CO>O>[OH:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]1[CH:7]=[C:6]([CH:5]([CH3:20])[C:4]([OH:21])=[O:3])[CH:18]=[CH:17][C:16]2=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 54544615HCID 54544615, compound

Product 1

HCID 199357086-Hydroxy-a-methyl carbazole-2-acetic acidYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture consisting of 6-hydroxy-α-methyl carbazole-2-acetic acid ethyl ester (5.0 g, 0.021 mol), potassium hydroxide (5.0 g, 0.089 mol), methanol (300 mL), and water (20 mL) is refluxed for 15 hours. The reaction mixture is cooled concentrated and acidified with a 1:1 solution of concentrated HCl and water to pH 1. The aqueous layer is extracted with ether (4×300 mL), washed with water (200 mL), brine (200 mL), dried over MgSO4, filtered and concentrated to give 2.6 g of product as a foam.

Workup

  1. temperatureis refluxed for 15 hours
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated
  4. extractionThe aqueous layer is extracted with ether (4×300 mL)
  5. washwashed with water (200 mL), brine (200 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3c89545c8f3f47e8b06fa48fd4267646
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Reaction notes

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