4-Chloro-3-hydrazinylbenzoic acid hydrochloride → 8-Chloro-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

HRID 1637258Notes

Reaction equation

HRID 1637258 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[CH:7][C:8]([Cl:13])=[C:9]([NH:11]N)[CH:10]=1)([OH:4])=O.[C:14]([CH:22]([CH2:26][CH3:27])C(O)=O)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[Cl:13][C:8]1[C:9]2[NH:11][C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:22]3[CH2:26][CH2:27][C:2](=[O:4])[C:5]([C:10]=23)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 162429964-Chloro-3-hydrazinylbenzoic acid hydrochlorideHCID 21651867alpha-Ethyl-beta-oxobenzenepropanoic acid

Product 1

HCID 193481908-Chloro-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-oneYield 107.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(5-carboxy-2-chlorophenyl)hydrazine hydrochloride (46 g) and benzoylbutyric acid (39.6 g) were suspended in water (500 ml) and the suspension was heated to reflux for 1 hour and allowed to cool. The crystals precipitated were collected by filtration, washed with methanol and ether, and air-dried to yield 62.4 g (84%) of the titled compound as pale brown crystals.

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for 1 hour
  3. temperatureto cool
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with methanol and ether
  7. customair-dried

Sources & evidence

ORD record
ord-ab3b249d3fff4fddb4cb3002cb14dd52
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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