HCID 67354024, compound → 5-Amino-2-hydroxy-N-methylbenzamide

HRID 522873Notes

Reaction equation

HRID 522873 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:10]=1[C:11]([NH:13][CH3:14])=[O:12])C1C=CC=CC=1>[Pd].CO>[NH2:19][C:16]1[CH:17]=[CH:18][C:9]([OH:8])=[C:10]([CH:15]=1)[C:11]([NH:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 67354024HCID 67354024, compound

Product 1

HCID 198229045-Amino-2-hydroxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a flask charged with 2-(benzyloxy)-N-methyl-5-nitrobenzamide (176 mg, 1.061 mmol) was added MeOH (4 mL). The resulting suspension was thoroughly purged with nitrogen prior to the addition of 10% Pd/C (12 mg, 0.046 mmol). The reaction mixture was purged with H2 gas, and then stirred under at atmosphere of hydrogen overnight. The reaction mixture was filtered through Celite® (diatomaceous earth) and the filtrate dried under reduced pressure. The resulting 5-amino-2-hydroxy-N-methylbenzamide (90 mg, 99% crude yield) was used in next step without further purification.

Workup

  1. customThe resulting suspension was thoroughly purged with nitrogen
  2. customThe reaction mixture was purged with H2 gas
  3. filtrationThe reaction mixture was filtered through Celite® (diatomaceous earth)
  4. customthe filtrate dried under reduced pressure
  5. customThe resulting 5-amino-2-hydroxy-N-methylbenzamide (90 mg, 99% crude yield) was used in next step without further purification

Sources & evidence

ORD record
ord-e7562d999bc24e8182f7d9f22f68fc9c
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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