Hydrazine → HCID 53976126, compound

HRID 273677Notes

Reaction equation

HRID 273677 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([C@@:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([OH:12])[C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)([O-])=O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:20]=[CH:19][C:7]([C@@:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([OH:12])[C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 12075632HCID 12075632, compound

Product 1

HCID 53976126HCID 53976126, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of (R)-4-nitrobenzilic acid (2.0 g, 7.33 mmol) in ethanol (25 ml) was treated with hydrazine (1.0 ml) and Raney-Ni (0.8 g) and stirred at room temperature for 18 hours under a nitrogen atmosphere. The Raney-Ni powder was removed by filtration, washed with ethanol, the ethanol layer concentrated to a small volume and diluted with water (75 ml). The aqueous layer was extracted with ether (2×50 ml) and the aqueous layer was evaporated under vacuum to provide a light yellow solid of (R)-4-aminobenzilic acid in 82% yield (1.46 g); mp 139°-140° C. (decomp); TLC [silica gel, acetone] Rf 0.20; 1NMR (D2O) δ6.75 and 7.18 (2d, 4H, C6H4) and 7.31 (s, 5H, C6H5).

Workup

  1. customThe Raney-Ni powder was removed by filtration
  2. washwashed with ethanol
  3. concentrationthe ethanol layer concentrated to a small volume
  4. additiondiluted with water (75 ml)
  5. extractionThe aqueous layer was extracted with ether (2×50 ml)
  6. customthe aqueous layer was evaporated under vacuum

Sources & evidence

ORD record
ord-a43809e69a9349278559c14d5ad9f2aa
Source dataset
uspto-grants-1995_02
Patent number
US05387409

Reaction notes

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