Hydrochloric Acid → Ethyl 5-(4-Aminophenyl)-2-Methyl-3-Furoate

HRID 393277Notes

Reaction equation

HRID 393277 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl>CCO.[Fe]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:4]2[O:3][C:2]([CH3:1])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2742183Ethyl 2-methyl-5-(4-nitrophenyl)furan-3-carboxylate

Product 1

HCID 2742184Ethyl 5-(4-Aminophenyl)-2-Methyl-3-FuroateYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-methyl-5-(4-nitrophenyl)-3-furanecarboxylate (500 mg, 1.82 mmol), iron powder (325 mesh, 811 mg, 14.5 mmol) and aqueous 1 N HCl solution (0.36 mL, 0.36 mmol) in EtOH (5 mL) was heated to reflux for 2 h. The reaction mixture was filtered and concentrated under reduced pressure to give the title compound (396 mg, 89% yield) as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7b722fe2a1748cf9baac49ab36e8f4f
Source dataset
uspto-grants-2004_10
Patent number
US06806265B2

Reaction notes

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