HCID 14479916, compound → HCID 178469348, compound

HRID 1762983Notes

Reaction equation

HRID 1762983 reaction equation
[CH3:1][C:2]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]2[C:5](=[CH:6][C:7]([NH:14][C:15]([C:17]3[CH:22]=[N:21][CH:20]=[CH:19][N:18]=3)=O)=[C:8]([N+:11]([O-])=O)[CH:9]=2)[NH:4][C:3]1=[O:23]>[Pd].C(O)C>[CH3:1][C:2]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]2[C:5](=[CH:6][C:7]3[NH:14][C:15]([C:17]4[CH:22]=[N:21][CH:20]=[CH:19][N:18]=4)=[N:11][C:8]=3[CH:9]=2)[NH:4][C:3]1=[O:23]

Participants

4

Reactant 1

HCID 14479916HCID 14479916, compound

Product 1

HCID 178469348HCID 178469348, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

3.2 g. (8.3 mmol) 3-methyl-3-ethoxycarbonyl-5-nitro-6-(2-pyrazinoylamino)-indolin-2-one in 100 ml. ethanol are hydrogenated in 100 ml. ethanol in the presence of 0.5 g. 10% palladium on charcoal. After completion of the take up of hydrogen, the solution is filtered off from the catalyst, the ethanol is evaporated off and the residue is stirred for 1 hour in glacial acetic acid at 60° C. The glacial acetic acid is evaporated, the residue is taken up in water, filtered and recrystallized from ethanol. There are obtained 1.8 g (65% of theory) of the title compound, m.p. 288°-290° C.

Workup

  1. filtrationAfter completion of the take up of hydrogen, the solution is filtered off from the catalyst
  2. customthe ethanol is evaporated off
  3. customThe glacial acetic acid is evaporated
  4. filtrationfiltered
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c687f0adcae04df2bd9f91fe7d37e1cd
Source dataset
uspto-grants-1989_05
Patent number
US04835280

Reaction notes

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