Water → Methyl 2-amino-4-ethoxy-5-methoxybenzoate

HRID 612117Notes

Reaction equation

HRID 612117 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([N+:16]([O-])=O)[CH:5]=1)[CH3:2].[Cl-].[NH4+].O>[Fe].CO>[NH2:16][C:6]1[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:13]([O:14][CH3:15])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium Chloride2×HCID 10491210Methyl 4-ethoxy-5-methoxy-2-nitrobenzoate

Product 1

HCID 10489373Methyl 2-amino-4-ethoxy-5-methoxybenzoateYield 82.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 24.110 g (94.5 mmol) methyl 4-ethoxy-5-methoxy-2-nitrobenzoate, 15.81 g (283 mmol) iron powder, 25.28 g (472 mmol) ammonium chloride, 135 ml water, and 350 ml methanol was heated to reflux under N2. At both 3 and 5.5 hours added the same amount of iron and ammonium chloride. Removed heat at 6.5 hours, added ethyl acetate and saturated sodium bicarbonate, filtered through celite and separated layers. Washed organic layer with saturated sodium bicarbonate, dried with magnesium sulfate, stripped solvent, and dried in vacuo, giving 17.594 g of pink solid: mass spectrum (electrospray m/e): M+H=226.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 6.5 hours
  5. additionadded ethyl acetate and saturated sodium bicarbonate
  6. filtrationfiltered through celite
  7. customseparated layers
  8. dry with materialWashed organic layer with saturated sodium bicarbonate, dried with magnesium sulfate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b1ebd82a65424d61b8d06145fd9dbf99
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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