8-Hydroxyquinoline → 6-Chloro-2,3-dihydro-1h-indole

HRID 1598006Notes

Reaction equation

HRID 1598006 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH2:6].OC1C=CC=C2C=1N=CC=C2.NN>C(O)CC(C)C>[Cl:11][C:9]1[CH:8]=[C:7]2[C:3]([CH2:4][CH2:5][NH:6]2)=[CH:2][CH:10]=1

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 9321HydrazineHCID 1429382,4-Dichlorophenethylamine

Product 1

HCID 2585676-Chloro-2,3-dihydro-1h-indole

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

This material was conveniently prepared on multigram scale from the cyclization of 2,4-dichlorophenethylamine in the presence of Na2 CO3 (s) (1.2 mol eq), Cu2Cl2 (0.01 mol eq) and 8-hydroxyquinoline (0.012 mol eq) in isoamyl alcohol (1 vol) at 130° C. for 5 hours. After addition of hydrazine (0.0055 vol) and 1 hour reflux, the mixture was filtered, solvent was removed in vacuo (45° C. @ ~10 mm Hg) and 6-chloro-indoline was obtained pure by vacuum distillation (95°-100° C. @ 2 mm Hg)(65-95%).

Workup

  1. temperaturereflux
  2. filtrationthe mixture was filtered
  3. customsolvent was removed in vacuo (45° C. @ ~10 mm Hg)

Sources & evidence

ORD record
ord-fd37b1ccb94c481097907e05c6204ecb
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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