HCID 13629298, compound → 2-(3-Amino-4-benzyloxyphenyl)acetic acid dipropylamide

HRID 1032509Notes

Reaction equation

HRID 1032509 reaction equation
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5](=[O:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([N+:21]([O-])=O)[CH:8]=1)[CH2:2][CH3:3].[H][H]>[Ni].CO>[CH2:25]([N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([NH2:21])[CH:8]=1)[CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 13629298HCID 13629298, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136292992-(3-Amino-4-benzyloxyphenyl)acetic acid dipropylamideYield 73.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In the presence of Raney nickel, 36.0 g of 2-(4-benzyloxy-3-nitrophenyl)acetic acid dipropylamide is hydrogenated in 600 ml of methanol until 6.7 l of hydrogen has been absorbed, which takes about 4.5 hours. The crude product obtained after removing the catalyst by filtration and after evaporation is chromatographed on silica gel with cyclohexane/ethyl acetate (1:1), thus obtaining 24.4 g of pure 2-(3-amino-4-benzyloxyphenyl)acetic acid dipropylamide as an oil.

Workup

  1. customhas been absorbed
  2. customThe crude product obtained
  3. customafter removing the catalyst
  4. filtrationby filtration
  5. customafter evaporation
  6. customis chromatographed on silica gel with cyclohexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-738ee511f8344515839a0616d119ba45
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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