Ammonia → 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-2-carboxamide

HRID 436511Notes

Reaction equation

HRID 436511 reaction equation
C[O:2][C:3]([CH:5]1[CH2:17][CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([Cl:18])[CH:13]=3)[NH:8][C:7]=2[CH2:6]1)=O.[NH3:19]>CO>[Cl:18][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[CH2:6][CH:5]([C:3]([NH2:19])=[O:2])[CH2:17][CH2:16][C:15]2=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21452693HCID 21452693, compound

Product 1

HCID 115361136-chloro-2,3,4,9-tetrahydro-1H-carbazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.5 g. of methyl-6-chloro-1,2,3,4-tetrahydrocarbazole-2-carboxylate, 20 g. of liquid ammonia and 150 ml. of methanol was placed in a pressure bottle. The mixture was shaken at 60° for 40 hours (internal pressure 60 lb/in2). Upon cooling to room temperature, the mixture was concentrated to dryness yielding 2.1 g. of product. Following a crystallization from ethyl acetate, 0.8 g. of 6-chloro-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid amide was obtained, m.p. 203°-204°.

Workup

  1. additionA mixture of 2.5 g
  2. concentrationthe mixture was concentrated to dryness
  3. customyielding 2.1 g
  4. customa crystallization from ethyl acetate, 0.8 g

Sources & evidence

ORD record
ord-7b3564bf279046fc87c2c6fb6abf9501
Source dataset
uspto-grants-1977_02
Patent number
US04009181

Reaction notes

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