HCID 178482126, compound → HCID 178482125, compound

HRID 485759Notes

Reaction equation

HRID 485759 reaction equation
[CH3:1][NH:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([N+:16]([O-])=O)=[CH:13][CH:14]=2)[C:9]([OH:19])=[N:8]1)=[O:6]>[Pd].CCO>[CH3:1][NH:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[C:5]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([NH2:16])=[CH:13][CH:14]=2)[C:9]([OH:19])=[N:8]1)=[O:6]

Participants

4

Reactant 1

HCID 178482126HCID 178482126, compound

Product 1

HCID 178482125HCID 178482125, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 1.5 g. of 1-(2-methylaminobenzoyl)-5-nitro-1H-indazol-3-ol, prepared in Example 19, suspended in 500 ml. of absolute EtOH was added 1.0 g. of 5% Pd/C and the mixture was hydrogenated at 50 psi for 20 hours. The catalyst was filtered off, washed with absolute EtOH and the filtrate evaporated to afford a semi-solid. Recrystallization from EtOH afforded 0.48 g. (35.4%) of the amine as a tan amorphous powder; mp. 169°-170° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with absolute EtOH
  3. customthe filtrate evaporated
  4. customto afford a semi-solid
  5. customRecrystallization from EtOH
  6. customafforded 0.48 g

Sources & evidence

ORD record
ord-9a36060f4aaf4865a17e9cf022ee4b9d
Source dataset
uspto-grants-1985_08
Patent number
US04537966

Reaction notes

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