HCID 13000592, compound → Ethyl 2-amino-6-methylbenzoate

HRID 1651001Notes

Reaction equation

HRID 1651001 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([N+:13]([O-])=O)[CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.C(O)C.O.[Fe]>[NH2:13][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 1

HCID 13000592HCID 13000592, compound

Product 1

HCID 15617258Ethyl 2-amino-6-methylbenzoate

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A reaction mixture of 185 g of ethyl 6-methyl-2-nitrobenzoate and 176 g of powdered iron in 343 mL of glacial acetic acid and 2200 mL of ethanol was heated at reflux for 5 hours. The reaction mixture was allowed to cool, diluted with excess water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated to an orange oil 148.3 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an orange oil 148.3 g

Sources & evidence

ORD record
ord-30b7f14ea9e4410f82ab57807a24ad3a
Source dataset
uspto-grants-1990_05
Patent number
US04927453

Reaction notes

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