Acetic Acid → 6-Benzyloxy-a-methyl-1,2,3,4-tetrahydrocarbazole-2-acetic acid ethyl ester

HRID 37709

Reaction equation

HRID 37709 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16]N)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:18][CH:19]([CH:23]1[CH2:28][CH2:27][CH2:26][C:25](=O)[CH2:24]1)[C:20]([OH:22])=[O:21].[C:30](O)(=O)[CH3:31]>O>[CH2:30]([O:22][C:20](=[O:21])[CH:19]([CH3:18])[CH:23]1[CH2:28][CH2:27][C:26]2[C:14]3[C:13](=[CH:12][CH:11]=[C:10]([O:9][CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[CH:15]=3)[NH:16][C:25]=2[CH2:24]1)[CH3:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochlorideHCID 57367081a-Methyl-3-oxocyclohexane acetic acid

Product 1

HCID 538233606-Benzyloxy-a-methyl-1,2,3,4-tetrahydrocarbazole-2-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 4-benzyloxyphenylhydrazine hydrochloride (37.0 g, 0.148 mol), a-methyl-3-oxocyclohexane acetic acid (40.0 g, 0.235 mol), glacial acetic acid (650 mL) and H2O (100 mL) is stirred at room temperature under a nitrogen atmosphere for 2.5 hours. The mixture is then refluxed for 20 minutes, cooled and poured into 200 mL of ice/H2O. The precipitate is filtered to give 80 g of red colored crude product.

Workup

  1. temperatureThe mixture is then refluxed for 20 minutes
  2. temperaturecooled
  3. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-4b025cac112b49168dfc24a172f3c62e
Source dataset
uspto-grants-1995_05
Patent number
US05420289

Linked notes

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