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Acetaldehyde → 9-Benzoyl-8-bromo-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid

HRID 1605099
Notes
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Reaction equation

HRID 1605099 reaction equation
[C:1]([N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Br:19])N=CC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1C=CC=CC=1NN=CC.[CH2:31]1[CH:37]([C:38]([OH:40])=[O:39])[CH2:36][CH2:35][C:33](=O)[CH2:32]1.C(=O)C.Cl>O.C(O)(=O)C>[C:1]([N:9]1[C:33]2[CH2:32][CH2:31][CH:37]([C:38]([OH:40])=[O:39])[CH2:36][C:35]=2[C:18]2[C:13]1=[C:14]([Br:19])[CH:15]=[CH:16][CH:17]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 1927304-Oxocyclohexanecarboxylic acidHCID 68139504Acetaldehyde 1-benzoyl-1-(2-bromophenyl)hydrazoneHCID 86733215Acetaldehyde 2-bromophenyl hydrazone

Product 1

HCID 215486279-Benzoyl-8-bromo-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of acetaldehyde 1-benzoyl-1-(2-bromophenyl)hydrazone, prepared from 11 g. of acetaldehyde 2-bromophenyl hydrazone (see below), and 9.16 g. of cyclohexanone-4-carboxylic acid in 25 ml. glacial acetic acid was heated on a hot plate until evolution of acetaldehyde was no longer detected (about two hours), 25 ml. glacial acetic acid saturated with hydrogen chloride was added and heating was continued for 30 minutes. The mixture was cooled and cautiously diluted with water, and the resulting solid was collected by filtration and washed with water to give 2.24 g. of the title compound; m.p. 196°-198°C. (chloroform-heptane).

Workup

  1. custom(about two hours), 25 ml
  2. temperatureheating
  3. temperatureThe mixture was cooled
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with water
  6. customto give 2.24 g

Sources & evidence

ORD record
ord-f6ccce52625749f6b08db8e5fc5078c1
Source dataset
uspto-grants-1976_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03948939

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes