Hydrazine → HCID 69435288, compound

HRID 916176Notes

Reaction equation

HRID 916176 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]([OH:21])=[O:20])=[CH:6][CH:5]=1)([O-])=O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]([OH:21])=[O:20])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 12377925HCID 12377925, compound

Product 1

HCID 69435288HCID 69435288, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A large excess of Raney® nickel was added in portions to a stirred solution of 1-(4-nitrophenyl)-1H-indole-2-carboxylic acid (1.40 g, 5.0 mmol), hydrazine (1.0 mL, 32 mmol) in 20 mL of ethanol. After stirring at room temperature for 2 h the catalyst was then removed by filtering through a short pad of Celite®521. The filtrate was concentrated to give 1-(4-aminophenyl)-1H-indole-2-carboxylic acid (1.0 g, 80%) as a beige solid: MS (ESI) m/z 253 (MH+); MS (ESI) m/z 251 ([M−H]−).

Workup

  1. customwas then removed
  2. filtrationby filtering through a short pad of Celite®521
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b1058c2d3a5644c6b38ada9330f7cebc
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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