Hydrochloric Acid → Methyl 3-amino-4-formylbenzoate

HRID 50364Notes

Reaction equation

HRID 50364 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N+:13]([O-])=O)=[O:2].Cl>[Fe].C(O)C>[NH2:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[CH:1]=[O:2])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3457222Methyl 4-formyl-3-nitrobenzoate

Product 1

HCID 18412577Methyl 3-amino-4-formylbenzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 25 mL of ethanol/glacial acetic acid/water (2:2:1) were added 0.6 g (2.9 mmol) of methyl 4-formyl-3-nitrobenzoate, 1.2 g (21.4 mmol) of iron powder and 0.01 mL of concentrated hydrochloric acid and the mixture was refluxed with stirring for 15 minutes. Then the iron was separated off, the solution was diluted with water and extracted with methylene chloride. The combined organic extracts were washed with water, dried, and evaporated down. Yield: 0.3 g (58% of theory); Rf value: 0.74 (silica gel, methylene chloride/methanol=9.5:0.5).

Workup

  1. temperaturethe mixture was refluxed
  2. customThen the iron was separated off
  3. additionthe solution was diluted with water
  4. extractionextracted with methylene chloride
  5. washThe combined organic extracts were washed with water
  6. customdried
  7. customevaporated down

Sources & evidence

ORD record
ord-692af410b2004b348d6a6e5e7c4983c5
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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