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

HRID 1679271Notes

Reaction equation

HRID 1679271 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.B(F)(F)F.F>[Pd].C(O)C>[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

5

Reactant 2

HCID 965023-PhenylindoleHCID 9855450Trifluoroborane Hydrofluoride

Product 1

HCID 109323533-phenyl-2,3-dihydro-1H-indoleYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.0 g of 3-phenylindole, 80 ml of 86% ethanol, 35 ml of 48% hydrofluoroboric acid and 0.25 g of 10% Pd/C was hydrogenated at 60 p.s.i. and 60° C for 18 hours. The reaction mixture was worked up as in Example 2 and 1.9 g of pure 3-phenylindoline was obtained.

Sources & evidence

ORD record
ord-c10a8c70d8c3481a80efa4c529c0a0f2
Source dataset
uspto-grants-1978_03
Patent number
US04080330

Reaction notes

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