Water → 1H-Indole, 6-methyl-

HRID 1798022Notes

Reaction equation

HRID 1798022 reaction equation
[C:1]([CH:3]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[N+:21]([O-])=O)C(OCC1C=CC=CC=1)=O)#N.O>[Pd].C(O)C>[CH3:20][C:17]1[CH:16]=[C:15]2[C:14]([CH:3]=[CH:1][NH:21]2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 962WaterHCID 10935797Benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate

Product 1

HCID 1379281H-Indole, 6-methyl-Yield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

a mixture of benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate (13 mmol), 5% palladium (0.84 g), water (4 mL) and ethanol (40 mL) is hydrogenated under 50 psi for 18 hours at 25° C. The catalyst is eliminated by filtration on celite and the solid is washed with ethanol. The filtrate obtained is evaporated under vacuum and the residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 2/1) in order to produce 6-methylindole with a yield of 74%.

Workup

  1. filtrationThe catalyst is eliminated by filtration on celite
  2. washthe solid is washed with ethanol
  3. customThe filtrate obtained
  4. customis evaporated under vacuum
  5. customthe residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 2/1) in order

Sources & evidence

ORD record
ord-d89ffe2ad0ef44d999e2bc5fb2b3c936
Source dataset
uspto-grants-2013_01
Patent number
US08343964B2

Reaction notes

Loading…