HCID 957454, compound → Benzyl 3-amino-2-methylbenzoate

HRID 2423233Notes

Reaction equation

HRID 2423233 reaction equation
[CH3:1][C:2]1[C:17]([N+:18]([O-])=O)=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]>[Fe].C(O)(=O)C>[NH2:18][C:17]1[C:2]([CH3:1])=[C:3]([CH:14]=[CH:15][CH:16]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

4

Reactant 1

HCID 957454HCID 957454, compound

Product 1

HCID 54141052Benzyl 3-amino-2-methylbenzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Iron powder was added to an acetic acid solution of benzyl 2-methyl-3-nitrobenzoate, followed by stirring at room temperature for 1.5 hours. The insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure. This was diluted with ethyl acetate, neutralized with an aqueous saturated sodium hydrogencarbonate solution, and the insoluble matter was separated by filtration. The filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Ethyl acetate was added and a solution of 4 M hydrogen chloride/ethyl acetate was dropwise added thereto at 0° C. The precipitate was collected by filtration to obtain benzyl 3-amino-2-methylbenzoate.

Workup

  1. customThe insoluble matter was separated by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThis was diluted with ethyl acetate
  4. customthe insoluble matter was separated by filtration
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. additionEthyl acetate was added
  10. additiona solution of 4 M hydrogen chloride/ethyl acetate was dropwise added
  11. customat 0° C
  12. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-6f99efb9a26041f89d3938286a5ef0bf
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

Loading…