Hydrochloric Acid → 2-Amino-3-methoxybenzaldehyde

HRID 1167175Notes

Reaction equation

HRID 1167175 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-])=O)=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].Cl>C(O)C.C(O)(=O)C.O.[Fe]>[CH3:1][O:2][C:3]1[C:4]([NH2:11])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 988673-Methoxy-2-nitrobenzaldehyde

Product 1

HCID 139701212-Amino-3-methoxybenzaldehydeYield 112.6%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

5 g of 3-methoxy-2-nitrobenzaldehyde are dissolved in a solution of 100 ml of ethanol, 100 ml of acetic acid and 50 ml of water. After addition of 11.4 g of iron and of 1.4 ml of concentrated hydrochloric acid, the reaction medium is heated at reflux for 10-15 minutes. After having cooled the reaction medium, 150 ml of water are added and the reaction mixture is extracted with 3×200 ml of dichloromethane. The organic phases are combined, washed with 500 ml of a saturated sodium hydrogencarbonate solution, dried over magnesium sulfate, filtered and evaporated under vacuum to provide 4.7 g of 3-methoxy-2-aminobenzaldehyde in the form of a colorless oil, used without purification in the following stage. (Yield: quantitative)

Workup

  1. temperatureat reflux for 10-15 minutes
  2. additionare added
  3. extractionthe reaction mixture is extracted with 3×200 ml of dichloromethane
  4. washwashed with 500 ml of a saturated sodium hydrogencarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-bdc97d47f63e4ce1bfc15a2bf8443b97
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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