HCID 178482203, compound → HCID 178482196, compound

HRID 485753Notes

Reaction equation

HRID 485753 reaction equation
[CH3:1][NH:2][C:3]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:4]=1[C:5]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[N:8]1)=[O:6]>CCO.[Pd]>[CH3:1][NH:2][C:3]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:4]=1[C:5]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[N:8]1)=[O:6]

Participants

4

Reactant 1

HCID 178482203HCID 178482203, compound

Product 1

HCID 178482196HCID 178482196, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 1.1 g. of 1-(2-methylamino-5-nitrobenzoyl)-1H-indazol-3-ol, prepared in Example 14, suspended in 200 ml of absolute EtOH was added 200 mg of 5% Pd/C and the mixture was hydrogenated at 50 psi for 16 hours. The catalyst was filtered off, washed with hot EtOH and the filtrate was diluted with H2O and concentrated to small volume. The precipitate was collected, washed with cold 95% EtOH and dried; yield of dark-yellow amorphous powder 0.65 g. (65.4%); m.p. 184°-186° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with hot EtOH
  3. additionthe filtrate was diluted with H2O
  4. concentrationconcentrated to small volume
  5. customThe precipitate was collected
  6. washwashed with cold 95% EtOH
  7. customdried

Sources & evidence

ORD record
ord-2e1ea073a0d54675ae6a193630976836
Source dataset
uspto-grants-1985_08
Patent number
US04537966

Reaction notes

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