Hydrochloric Acid → methyl 4-(3-aminophenyl)benzoate

HRID 2230979Notes

Reaction equation

HRID 2230979 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(=O)(O)[O-].[Na+]>CO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2753361Methyl 3'-nitro[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 1393986methyl 4-(3-aminophenyl)benzoateYield 72.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(3-nitrophenyl)benzoate (8.37 g), iron powder (7.5 g) and hydrochloric acid (35%, 22 ml) in methanol (60 ml) was stirred under reflux for 3 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give methyl 4-(3-aminophenyl)benzoate (5.33 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-99d54239d1bc40a287836275f1dddf09
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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