HCID 20064141, compound → HCID 58376029, compound

HRID 1660837Notes

Reaction equation

HRID 1660837 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([OH:13])=[C:6]([Cl:14])[CH:5]=1>CO.O.[Fe]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[C:6]([Cl:14])[C:7]([OH:13])=[C:8]([NH2:10])[CH:9]=1

Participants

5

Reactant 1

HCID 20064141HCID 20064141, compound

Product 1

HCID 58376029HCID 58376029, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-chloro-4-hydroxy-5-nitro-benzoic acid methyl ester (500 mg, 2.16 mmol) in methanol (22 mL) was added within 10 min to a mixture of iron powder (410 mg, 7.34 mmol) ammonium chloride (647 mg, 12.1 mmol) in water (22 mL). The reaction mixture was heated at reflux over 16 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was extracted with ethyl acetate, dried (MgSO4), and evaporated. Chromatography (SiO2, ethyl acetate/heptane 7:3) afforded 3-amino-5-chloro-4-hydroxy-benzoic acid methyl ester (293 mg, 68%). Light yellow solid, MS (ISP)=200.1 (M−H)−.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux over 16 h
  3. temperatureafter cooling
  4. filtrationfiltered through a pad of diatomaceous earth
  5. extractionThe filtrate was extracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-7eeaa773d2394dcaa198b6339913a628
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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