3-Phenylindole → 3-phenyl-2,3-dihydro-1H-indole

HRID 1679272Notes

Reaction equation

HRID 1679272 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>Cl.[Zn]>[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 965023-Phenylindole

Product 1

HCID 109323533-phenyl-2,3-dihydro-1H-indole

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

1.3 G of 3-phenylindole was suspended in 100 ml of 20% aqueous hydrochloric acid. The mixture was heated to 60° C while stirring vigorously and 20 g of zinc dust was added thereto in small portions over a period of 45 minutes. On completing the addition of zinc dust, the reaction mixture was heated to 100° C and maintained at this temperature for one hour, filtered hot, and the filtrate cooled to room temperature and washed with ether. The aqueous layer was basified with 50% aqueous sodium hydroxide and the desired product was extracted with ether and then purified by column chromatography using silica gel. The 3-phenylindoline was obtained in a yield of 0.8 g as a yellow viscous oil.

Workup

  1. temperaturethe reaction mixture was heated to 100° C
  2. temperaturemaintained at this temperature for one hour
  3. filtrationfiltered hot
  4. temperaturethe filtrate cooled to room temperature
  5. washwashed with ether
  6. extractionthe desired product was extracted with ether
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-c0bbd64fb6cd46ef8d5c9ba77cc28168
Source dataset
uspto-grants-1978_03
Patent number
US04080330

Reaction notes

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