Hydrazine hydrate (1:1) → HCID 58653708, compound

HRID 1676036Notes

Reaction equation

HRID 1676036 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][NH:8][C:9]2[C:10]([N+:27]([O-])=O)=[C:11]([CH:24]=[CH:25][CH:26]=2)[NH:12][CH:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][C:15]([OH:17])=[O:16])=[CH:5][CH:4]=1.O.NN>C(O)C.[Ni]>[NH2:27][C:10]1[C:9]([NH:8][CH2:7][C:6]2[CH:30]=[CH:31][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:26][CH:25]=[CH:24][C:11]=1[NH:12][CH:13]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58653672HCID 58653672, compound

Product 1

HCID 58653708HCID 58653708, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-{3-[(4-methoxybenzyl)amino]-2-nitroanilino}-3-phenylpropanoic acid (176 mg, 418 μmol) in ethanol (6 mL) was added Raney-nickel (Aldrich22, 167-8, catalytic, ca. 5 mg) and hydrazine hydrate (200 μL, 4.12 mmol). The resulting suspension was stirred at room temperature for 0.6 hour. The suspension was filtered through Celite®, and the pad washed with ethanol. The combined filtrates were evaporated in vacuo, and the residue purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (19:1) to afford the title compound, 1H NMR: (CD3OD), 7.76-7.74 (m, 1H), 7.66-7.61 (m, 1H), 7.41-7.20 (m, 7H), 6.91-6.87 (m, 2H), 6.50-6.46 (m, 1H), 6.23-6.21 (m, 1H), 6.07-6.05 (m, 1H), 4.81 (br t, J=6.59, 1H), 4.27-4.24 (m, 3H), 3.80 (s, 3H), 2.90 (dd, J=15.38, 8.79, 1H), 2.76 (dd, J=15.38, 9.89, 1H).

Workup

  1. filtrationThe suspension was filtered through Celite®
  2. washthe pad washed with ethanol
  3. customThe combined filtrates were evaporated in vacuo
  4. customthe residue purified by flash column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and methanol (19:1)

Sources & evidence

ORD record
ord-eaa3cb83eedb481eba5a6300f3d865f0
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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