Methanol → Benzoate

HRID 966097Notes

Reaction equation

HRID 966097 reaction equation
Cl.[OH:2][C:3]1[C:4]([O:20][CH3:21])=[C:5]([C:10](=[O:19])[CH2:11][NH:12][C:13]2([CH3:18])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=[CH:7][C:8]=1[OH:9].C[OH:23]>[Pt](=O)=O>[OH:19][CH:10]([C:5]1[C:4]([O:20][CH3:21])=[C:3]([OH:2])[C:8]([OH:9])=[CH:7][CH:6]=1)[CH2:11][NH:12][C:13]1([CH3:18])[CH2:14][CH2:15][CH2:16][CH2:17]1.[C:10]([O-:19])(=[O:23])[C:5]1[CH:4]=[CH:3][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 22314537HCID 22314537, compound

Product 2

HCID 242BenzoateHCID 10468929HCID 10468929, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

5 g of 1-(3,4-dihydroxy-2-methoxyphenyl)-2-(1-methylcyclopentylamino)ethanone hydrochloride is hydrogenated with 0.2 g of platinum(IV) oxide in 200 mL methanol. The catalyst is suction filtered and the solvent is distilled off under reduced pressure. The residue remaining is dissolved in ethanol and combined with 5 g of sodium benzoate. The title compound is isolated in the form of its benzoate. Yield: 4.5 g (70.5%; benzoate); melting point: 179° C.-180° C.

Workup

  1. filtrationfiltered
  2. distillationthe solvent is distilled off under reduced pressure
  3. dissolutionThe residue remaining is dissolved in ethanol

Sources & evidence

ORD record
ord-80d81f2795cb4fbea7fdd9ed30262f4b
Source dataset
uspto-grants-2005_10
Patent number
US06951888B2

Reaction notes

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