Water → Methyl (3-aminophenyl)carbamate

HRID 1033150Notes

Reaction equation

HRID 1033150 reaction equation
[Cl-].[NH4+].O.[CH3:4][O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([N+:15]([O-])=O)[CH:12]=[CH:13][CH:14]=1)=[O:7]>[Fe].CC(O)C>[CH3:4][O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[NH2:15])=[O:7]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4548185Methyl N-(3-nitrophenyl)carbamate

Product 1

HCID 12877207Methyl (3-aminophenyl)carbamateYield 95.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Procedure

After refluxing a mixture of 37 g of iron powder, 1.9 g of ammonium chloride, 33 g of water, 13 g of 3-(methoxycarbonylamino)nitrobenzene, and 260 g of 2-propanol for 30 minutes, the reaction mixture was filtered under suction using sellaite. After extracting the product formed from the filtrate with ethyl acetate followed by washing with water, the product was dried by Glauber's salt. The solvent was distilled off from the product using an evaporator to provide 10.5 g (yield: 95%) of a black oily product.

Workup

  1. temperatureAfter refluxing
  2. filtrationthe reaction mixture was filtered under suction
  3. extractionAfter extracting the product
  4. customformed from the filtrate with ethyl acetate
  5. washby washing with water
  6. dry with materialthe product was dried by Glauber's salt
  7. distillationThe solvent was distilled off from the product
  8. customan evaporator

Sources & evidence

ORD record
ord-559818628ca640d6b2a6ffe67d955ef0
Source dataset
uspto-grants-1994_05
Patent number
US05310634

Reaction notes

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