ethyl 2-(1-methyl-6,7-dihydro-1H-indol-4(5H)-ylidene)acetate → ethyl 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)acetate

HRID 447746Notes

Reaction equation

HRID 447746 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]=2[CH:4]=[CH:3]1>[Pd].CCO>[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]=2[CH:4]=[CH:3]1

Participants

4

Reactant 1

HCID 69074859ethyl 2-(1-methyl-6,7-dihydro-1H-indol-4(5H)-ylidene)acetate

Product 1

HCID 20761741ethyl 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)acetateYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd—C (1.3 g, 5%) is added to a solution of a mixture of E/Z isomers of ethyl 2-(1-methyl-6,7-dihydro-1H-indol-4(5H)-ylidene)acetate (3.4 g, 15.50 mmoles) in 100 mL de EtOH, and the resulting solution is stirred under hydrogen atmosphere (25 psi) in a Parr hydrogenator for 8 hours. The reaction mixture is purged with nitrogen, filtered through Celite and the solvent is evaporated under reduced pressure to obtain ethyl 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)acetate (3.4 g, 15.36 mmol, 99%, oil).

Workup

  1. customThe reaction mixture is purged with nitrogen
  2. filtrationfiltered through Celite
  3. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-611f8ae3c2ae462d852a598c16dbe7ff
Source dataset
uspto-grants-2013_07
Patent number
US08481567B2

Reaction notes

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