4-(Benzyloxy)-N-methoxy-N-methylbenzamide → 4-Hydroxy-N-methoxy-N-methylbenzamide

HRID 494827Notes

Reaction equation

HRID 494827 reaction equation
C([O:8][C:9]1[CH:20]=[CH:19][C:12]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:20]=[CH:19][C:12]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 113117774-(Benzyloxy)-N-methoxy-N-methylbenzamide

Product 1

HCID 113897574-Hydroxy-N-methoxy-N-methylbenzamideYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

10% Palladium on charcoal (4.5 g) in methanol (10 mL) was treated with the product from Example 71B (18.60 g, 68.55 mmol) in 150 mL methanol. The mixture was placed under hydrogen atmosphere at 67 psi. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography to provide the title compound (10.3 g, 83% yield). 1HNMR (300 MHz, CD3OD) δ 3.32 (s, 3H), 3.58 (s, 3H), 6.81 (d, 2H, J=8.9 Hz). 7.59 (d, 2H, J=8.9 Hz); MS (DCI) m/z 182 (M+H)+, 199 (M+NH4)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4082ed80f96841199d28a4de312bd312
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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