HCID 14749570, compound → HCID 14749571, compound

HRID 1110427Notes

Reaction equation

HRID 1110427 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([CH3:22])([CH3:21])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)=[O:10].[H][H]>CO.[Ni]>[NH2:18][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]([CH3:21])([CH3:22])[CH2:7][CH2:6][CH2:5][O:4][C:3]2[CH:23]=[C:24]([CH3:27])[CH:25]=[CH:26][C:2]=2[CH3:1])[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 14749570HCID 14749570, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14749571HCID 14749571, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

5-(2,5-Dimethylphenoxy)-2,2-dimethyl-N-(3-nitrophenyl)pentanamide (Example 1i), 22.39 g (0.0604 mol), is dissolved in 400 ml of methanol, 1.5 g of Raney nickel is added and the mixture is exposed to hydrogen gas until the required amount of hydrogen is absorbed. The methanol solution is filtered and concentrated in vacuo and the residue solidifes to afford 19.8 g of N-(3-aminophenyl)-5-(2,5-dimethylphenoxy)-2,2-dimethylpentanamide after recrystallization from isopropyl ether; mp 93°-94° C.

Workup

  1. customis absorbed
  2. filtrationThe methanol solution is filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-409cba252f9c40dfbf11c77719350f92
Source dataset
uspto-grants-1990_12
Patent number
US04975456

Reaction notes

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