Phenyl 2-(4-nitrophenoxy)benzoate → Phenyl 2-(4-aminophenoxy)benzoate

HRID 1982359Notes

Reaction equation

HRID 1982359 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=2[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=2[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 23316310Phenyl 2-(4-nitrophenoxy)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 23316308Phenyl 2-(4-aminophenoxy)benzoateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9 g of phenyl 2-(4'-nitrophenoxy)benzoate, prepared as described in Example 1, are contacted with hydrogen in 50 cm3 of ethanol, in the presence of 5% palladium (100 mg) on coal. After recrystallization in 100 cm3 of a methanol-water mixture (50--50 by volume), 7.52 g of phenyl 2-(4'-aminophenoxy)benzoate (m.p. 102° C.) are obtained (yield: 92%).

Workup

  1. customAfter recrystallization in 100 cm3 of a methanol-water mixture (50--50 by volume)

Sources & evidence

ORD record
ord-2b5f8d4c882940be86553507d73954d7
Source dataset
uspto-grants-1986_06
Patent number
US04596680

Reaction notes

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