Methanol → Methyl 5-amino-o-anisate

HRID 343486Notes

Reaction equation

HRID 343486 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].CO>[Pd].ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 887MethanolHCID 7020925Benzoic acid, 2-methoxy-5-nitro-, methyl ester

Product 1

HCID 89843Methyl 5-amino-o-anisate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine methyl 2-methoxy-5-nitrobenzoate (13.3 g, 63 mmol) and methanol. Add 5% palladium-on-carbon (0.66 g). Hydrogenate on a pressure apparatus at 50 psi. After 17 hours, filter through celite to remove the catalyst and evaporate the filtrate invacuo to give a residue. Combine the residue and dichloromethane and extract with water. Dry the organic layer over Na2SO4, filter, and evaporate invacuo to give methyl 2-methoxy-5-aminobenzoate. Rf =0.18 (silica gel, ethyl acetate/methanol 1/1). Elemental Analysis calculated for C9H11NO3 : C, 59.66; H, 6.12; N, 7.73. Found: C, 59.44; H, 6.04; N, 7.62.

Workup

  1. filtrationfilter through celite
  2. customto remove the catalyst
  3. customevaporate the filtrate invacuo
  4. customto give a residue
  5. extractionextract with water
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate invacuo

Sources & evidence

ORD record
ord-c2d9c4b08b1f4bc994faccb0d7f2b328
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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