HCID 19832373, compound → HCID 19832254, compound

HRID 2051535Notes

Reaction equation

HRID 2051535 reaction equation
[CH3:1][C:2]1([CH3:24])[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=3)=[O:12])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:23]>[Pd].CO>[CH3:1][C:2]1([CH3:24])[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=3)=[O:12])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:23]

Participants

4

Reactant 1

HCID 19832373HCID 19832373, compound

Product 1

HCID 19832254HCID 19832254, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.6 g. (8 mmol) 2,3-Dihydro-3,3-dimethyl-N-(4-nitrophenyl)-2-oxo-(1H)-indole-6-carboxamide (from Example 6) in 50 ml. methanol were hydrogenated in the presence of 0.3 g. 10% palladium on charcoal at normal pressure and ambient temperature. After 2 hours, the reaction mixture was filtered with suction, the solvent was removed from the filtrate in a vacuum and the residue purified by column chromatography (silica gel; elution agent dichloromethane/methanol saturated with ammonia 95:5 v/v). The solvent was removed in a vacuum, the residue was digested with ethyl acetate, filtered off with suction and the residue dried in a vacuum at 100° C. There was obtained 1.4 g. (61% of theory) of the title compound; m.p. 216°-218° C. The title compound contained adhering thereto 0.5 mole of water per mole.

Workup

  1. customat normal pressure and ambient temperature
  2. filtrationthe reaction mixture was filtered with suction
  3. customthe solvent was removed from the filtrate in a vacuum
  4. customthe residue purified by column chromatography (silica gel; elution agent dichloromethane/methanol saturated with ammonia 95:5 v/v)
  5. customThe solvent was removed in a vacuum
  6. filtrationfiltered off with suction
  7. customthe residue dried in a vacuum at 100° C
  8. customThere was obtained 1.4 g

Sources & evidence

ORD record
ord-e6cba360c1a34f76a49f0b71bf3654f5
Source dataset
uspto-grants-1991_05
Patent number
US05019587

Reaction notes

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