Hydrochloric Acid → Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoate

HRID 1934948Notes

Reaction equation

HRID 1934948 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:6][C:5]=1[N+:17]([O-])=O.[Cl-].[NH4+].O.Cl>[Fe].CO>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:6][C:5]=1[NH2:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 25517Ammonium ChlorideHCID 23032992Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate

Product 1

HCID 23033013Methyl 2-amino-4-(3-chloropropoxy)-5-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of 91 g (299.6 mmol) of 4-(3-chloro-propoxy)-5-methoxy-2-nitro-benzoic acid methyl ester and 55.2 g (988.8 mmol) of iron was mechanically stirred at reflux in a mixture containing 60.1 g ammonium chloride, 500 ml water, and 1300 ml methanol for 5.5 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 solvent was removed and the residue mixed with 300 ml of ether-hexane 2:1. After standing 73.9 g of the title compound was obtained as a pink solid: mass spectrum (electrospray, m/e): 2M−HCl+H 511.0; M+H 273.8

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. customThe solvent was removed
  8. additionthe residue mixed with 300 ml of ether-hexane 2:1
  9. customwas obtained as a pink solid

Sources & evidence

ORD record
ord-d21053f5f0024b0f829ad9fccb480619
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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