6-(Benzylamino)-1-isopropyl-3,3-dimethylindolin-2-one → 6-Amino-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 1507577Notes

Reaction equation

HRID 1507577 reaction equation
C([NH:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH3:23])([CH3:22])[C:14](=[O:21])[N:15]2[CH:18]([CH3:20])[CH3:19])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[NH2:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH3:23])([CH3:22])[C:14](=[O:21])[N:15]2[CH:18]([CH3:19])[CH3:20])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 900477036-(Benzylamino)-1-isopropyl-3,3-dimethylindolin-2-one

Product 1

HCID 900464376-Amino-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

Palladium on activated carbon (10%, 276 mg, 259 μmol) was added to a solution of 6-(benzylamino)-1-isopropyl-3,3-dimethylindolin-2-one (1.60 g, 5.18 mmol) in ethanol (75 ml). The mixture was stirred at room temperature under an hydrogen atmosphere (balloon) for 16 hours. As reaction was incomplete, the catalyst was filtered off and washed with ethanol. The solvent was evaporated and ethanol (75 ml) was added to the residue. Palladium on activated carbon (276 mg, 259 μmol) was added and hydrogenation (balloon) continued for 6 hours at 50° C. and 12 hours at room temperature. The catalyst was filtered off, washed with ethanol and the solvent was evaporated. The residue was purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as light yellow solid (892 mg).

Workup

  1. customAs reaction
  2. filtrationthe catalyst was filtered off
  3. washwashed with ethanol
  4. customThe solvent was evaporated
  5. additionethanol (75 ml) was added to the residue
  6. waithydrogenation (balloon) continued for 6 hours at 50° C. and 12 hours at room temperature
  7. filtrationThe catalyst was filtered off
  8. washwashed with ethanol
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-082104de4e8943f7b68d21cc6fd2991e
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

Loading…