Hydrazine hydrate (1:1) → HCID 20098375, compound

HRID 1768996Notes

Reaction equation

HRID 1768996 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:22])=[C:8]([CH:21]=1)[C:9]([NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2)=[O:10])([O-])=O.O.NN>[Ni].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([OH:22])=[C:8]([CH:21]=1)[C:9]([NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2)=[O:10]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14231066HCID 14231066, compound

Product 1

HCID 20098375HCID 20098375, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 6 g of 5-nitro-2-hydroxy-N-(1H-indol-4-yl)-benzamide of Example 50, 600 ml of methanol and 15 ml of 64% hydrazine hydrate and 6 g of Raney nickel was refluxed for two hours and filtered. The filtrate was evaporated to dryness under pressure at 50° C. and the residue was taken up in a 1-1 mixture of chloroform and methanol. The mixture was filtered and the crystalline product was dried to obtain 4 g of 5-amino-2-hydroxy-N-(1H-indol-4-yl)-benzamide melting at >260° C.

Workup

  1. temperaturewas refluxed for two hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness under pressure at 50° C.
  4. additionthe residue was taken up in a 1-1 mixture of chloroform and methanol
  5. filtrationThe mixture was filtered
  6. customthe crystalline product was dried

Sources & evidence

ORD record
ord-596850a84617451d87206e65f882791b
Source dataset
uspto-grants-1995_01
Patent number
US05380722

Reaction notes

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