HCID 66722704, compound → Benzoic acid, 3-(aminocarbonyl)-4-hydroxy-, methyl ester

HRID 1639533Notes

Reaction equation

HRID 1639533 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[C:19](=[O:21])[NH2:20])C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:19]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:9]=1[OH:8])[C:13]([O:15][CH3:16])=[O:14])(=[O:21])[NH2:20]

Participants

5

Reactant 2

HCID 66722704HCID 66722704, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10607886Benzoic acid, 3-(aminocarbonyl)-4-hydroxy-, methyl esterYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Hydrogenolysis is effected by dissolving 1.2 gm (4.2 mmol) of methyl 4-benzyloxy-3-carbamoylbenzoate in 60 mL of methanol (warmed to effect solution), adding 1 gm of 10% Pd/C (50% water) catalyst, and stirring under 48 psi of hydrogen overnight at room temperature. The reaction mixture is filtered, and the catalyst is repeatedly washed with 10% MeOH/DCM. The combined filtrates are evaporated to dryness to give 0.79 gm (4.05 mmol, 96% yield) of methyl 3-carbamoyl-4-hydroxybenzoate.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe catalyst is repeatedly washed with 10% MeOH/DCM
  3. customThe combined filtrates are evaporated to dryness

Sources & evidence

ORD record
ord-5657a81bc4a645d7b86e8a8ae20acb10
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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