HCID 21254723, compound → HCID 21254704, compound

HRID 636481Notes

Reaction equation

HRID 636481 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[C:10]=2[NH2:11])=[CH:5][CH:4]=1>C(O)(=O)C.C(O)C.[Fe]>[NH2:11][C:10]1[C:9]([O:8][CH2:7][C:6]2[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:16]

Participants

5

Reactant 1

HCID 21254723HCID 21254723, compound

Product 1

HCID 21254704HCID 21254704, compoundYield 84.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 2-(4-methoxybenzyloxy)-6-nitroaniline (3 g) in acetic acid (6 ml) and ethanol (24 ml) was added iron (3.06 g), and the mixture was refluxed for 3 hours. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. To the residue was added saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was pulverized with diethyl ether to give 2-amino-3-(4-methoxybenzyloxy)aniline (2.25 g).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. filtrationInsoluble material was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo the residue was added saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2ece39764a304d5a93b9ad2e5c3eeb58
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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