2-[5-(Benzyloxy)-2-nitroanilino]propionaldehyde dimethyl acetal → 2-[2-Amino-5-(benzyloxy)anilino]propionaldehyde dimethyl acetal

HRID 2293725Notes

Reaction equation

HRID 2293725 reaction equation
[CH3:1][O:2][CH:3]([O:24][CH3:25])[CH:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]=1[N+:21]([O-])=O)[CH3:5].[H][H]>O1CCCC1.[Ni]>[CH3:1][O:2][CH:3]([O:24][CH3:25])[CH:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]=1[NH2:21])[CH3:5]

Participants

5

Reactant 2

HCID 190831162-[5-(Benzyloxy)-2-nitroanilino]propionaldehyde dimethyl acetalHCID 178418361HCID 178418361, compound

Product 1

HCID 190831072-[2-Amino-5-(benzyloxy)anilino]propionaldehyde dimethyl acetal

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[5-(benzyloxy)-2-nitroanilino]propionaldehyde dimethyl acetal (24.0 g, 0.0715 mole) in tetrahydrofuran is treated with Raney nickel (10 g) and placed in a Parr shaker hydrogenation apparatus under 20.5-37 psig hydrogen at ambient temperature. After the uptake of the theoretical quantity of hydrogen, the mixture is filtered and the filtrate is concentrated in vacuo to afford the title product as a dark-colored syrup. The product is identified by infrared and mass spectral analyses.

Workup

  1. filtrationAfter the uptake of the theoretical quantity of hydrogen, the mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-1af903643f5347f498bdf71d9c0892fb
Source dataset
uspto-grants-1997_11
Patent number
US05686617

Reaction notes

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