Ammonium Chloride → Methyl 3-amino-5-(hydroxymethyl)benzoate

HRID 1531940Notes

Reaction equation

HRID 1531940 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[Cl-].[NH4+]>CO.O.[Fe]>[NH2:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([CH2:2][OH:1])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 10703703Methyl 3-(hydroxymethyl)-5-nitrobenzoate

Product 1

HCID 10535399Methyl 3-amino-5-(hydroxymethyl)benzoate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of the product from step (ii) (23.4 g), ammonium chloride (23 g) and iron powder (23 g) in methanol (200 ml) and water (200 ml) was heated at reflux for 1 hour. The mixture was filtered and concentrated under reduced pressure and the residue treated with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was dried (MgSO4) and evaporated. Yield 19.38 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. additionthe residue treated with saturated aqueous sodium bicarbonate
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract was dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-73be7f328e9a4c6b93b792fc8de42738
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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