Phenylmethyl 4-nitrobenzoate → Benzyl p-aminobenzoate

HRID 467801

Reaction equation

HRID 467801 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>O1CCOCC1.[Ni]>[NH2:1][C:4]1[CH:19]=[CH:18][C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 84647Phenylmethyl 4-nitrobenzoate

Product 1

HCID 98488Benzyl p-aminobenzoateYield 93.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

20.6 g of the benzyl 4-nitrobenzoate are dissolved in 350 mL dioxane and this solution is combined with 6.9 g (49.9 mmol, 0.61 eq) Raney nickel. The mixture is hydrogenated at 5 bar H2 pressure for 16 h with stirring. The catalyst is filtered off and all the volatile constituents are eliminated in vacuo. 17 g benzyl 4-aminobenzoate are obtained.

Workup

  1. filtrationThe catalyst is filtered off

Sources & evidence

ORD record
ord-089e658d436f4ff495a9757f8aaf70de
Source dataset
uspto-grants-2014_01
Patent number
US08623887B2

Linked notes

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