Water → Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate

HRID 1934949Notes

Reaction equation

HRID 1934949 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][Cl:15])=[CH:6][C:5]=1[N+:16]([O-])=O.[Cl-].[NH4+].O>[Fe].CO>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][Cl:15])=[CH:6][C:5]=1[NH2:16]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23032998Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoate

Product 1

HCID 23033001Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of 68.2 g (235.4 mmol) of 4-(2-chloro-ethoxy)-5-methoxy-2-nitro-benzoic acid methyl ester and 52.6 g (941.8 mmol) of iron was mechanically stirred at reflux in a mixture containing 62.9 g ammonium chloride, 393 ml water, and 1021 ml methanol for 15 hr. The mixture was concentrated and mixed with ethyl acetate. The organic solution was washed with water and saturated sodium bicarbonate. The solution was dried over magnesium sulfate and filtered through a short column of silica gel. The solution was concentrated to 200 ml and diluted with 250 of hot hexane. After standing 47.7 g of the title compound was obtained as a solid: mass spectrum (electrospray, m/e) M+H 259.8.

Workup

  1. temperatureat reflux in a mixture
  2. concentrationThe mixture was concentrated
  3. additionmixed with ethyl acetate
  4. washThe organic solution was washed with water and saturated sodium bicarbonate
  5. dry with materialThe solution was dried over magnesium sulfate
  6. filtrationfiltered through a short column of silica gel
  7. concentrationThe solution was concentrated to 200 ml
  8. additiondiluted with 250 of hot hexane
  9. customwas obtained as a solid

Sources & evidence

ORD record
ord-e542faff822a49838e49631329666516
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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