Ethyl indole-2-carboxylate → ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate

HRID 1596531Notes

Reaction equation

HRID 1596531 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)(=O)C.[Pt](=O)=O>[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 1

HCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 300702ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylateYield 33.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl indole-2-carboxylate (0.5 g) and platinum (IV) oxide (0.1 g) in acetic acid (20 ml) were stirred under an atmosphere of hydrogen for 16 hours at ambient temperature. The reaction was then filtered through a pad of celite and basified by addition of aqueous sodium hydroxide (2N). The resulting precipitate was filtered and dried in vacuo to give the product as a white solid (0.17 g, 33%), NMR d(CDCl3) 1.35 (3H, t), 1.80 (4H, m), 2.50 (2H, t), 2.60 (2H, t), 4.30 (2H, q), 6.65 (1H, d), 8.70 (1H, bs); M/z (+) 194 (MH+).

Workup

  1. filtrationThe reaction was then filtered through a pad of celite
  2. additionbasified by addition of aqueous sodium hydroxide (2N)
  3. filtrationThe resulting precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8decb82cc7644483946e1ffa87029e20
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Reaction notes

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