Methanol → Methyl 5-amino-o-anisate

HRID 1459594Notes

Reaction equation

HRID 1459594 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][CH3:14].CO.[H][H]>[Pt]=O.O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:13][CH3:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 7020925Benzoic acid, 2-methoxy-5-nitro-, methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 89843Methyl 5-amino-o-anisate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 2 liter Parr Bottle was charged with 11.6 grams (55 mmol) methyl-2-methoxy-5-nitrobenzoate, 450 mL of methanol and 150 mL of tetrahydrofuran (THF). Platinum oxide was added (460 mg) and the mixture was hydrogenated under 45 psi hydrogen for 1 hour. The reaction mixture was filtered through Celite® (diatomaceous earth) and evaporated. The reaction mixture was diluted with 500 mL of methylene chloride, and then washed with water and brine. The organic phase was dried and evaporated (9.9 grams). This material was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through Celite® (diatomaceous earth)
  2. customevaporated
  3. additionThe reaction mixture was diluted with 500 mL of methylene chloride
  4. washwashed with water and brine
  5. customThe organic phase was dried
  6. customevaporated (9.9 grams)
  7. customThis material was used without further purification

Sources & evidence

ORD record
ord-6e6468f9a95e409d9ab281afb5a89c99
Source dataset
uspto-grants-1998_12
Patent number
US05854262

Reaction notes

Loading…