5-(N-formyl-N-methylamino-methyl)-2-nitrobenzoic acid methyl ester → 2-amino-5-(N-formyl-N-methylamino-methyl)benzoic acid methyl ester

HRID 557449Notes

Reaction equation

HRID 557449 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([CH2:10][N:11]([CH:13]=[O:14])[CH3:12])[CH:7]=[CH:6][C:5]=1[N+:15]([O-])=O.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([CH2:10][N:11]([CH:13]=[O:14])[CH3:12])[CH:7]=[CH:6][C:5]=1[NH2:15]

Participants

5

Reactant 2

HCID 580183255-(N-formyl-N-methylamino-methyl)-2-nitrobenzoic acid methyl esterHCID 178418361HCID 178418361, compound2×

Product 1

HCID 580183322-amino-5-(N-formyl-N-methylamino-methyl)benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

There was dissolved, in 34 mL of methanol, 4.47 g of the crude product of 5-(N-formyl-N-methylamino-methyl)-2-nitrobenzoic acid methyl ester, prepare in the step 1, 5% Pd/C (wet product) was added to the solution in an argon gas atmosphere and then hydrogen gas was introduced into the reaction container. The reaction system was stirred at a reaction temperature of 40° C. for 8 hours, the hydrogen gas was replaced with argon gas, 14 mL of methanol was then added to the reaction system and the temperature thereof was raised up to 55° C. The Pd/C catalyst was removed through filtration under reduced pressure, the catalyst was washed with 25 mL of methanol and the resulting filtrate and the wash liquid were maintained at a temperature of 40° C. Water (31 mL) was dropwise added thereto thus separate out solid and the resulting slurry was stirred at 10° C. overnight. The resulting solid was separated from the slurry through filtration under reduced pressure, washed with 7 mL of water and then dried under reduced pressure at 70° C. for 5 hours to give 2.53 g of the title compound as a white solid.

Workup

  1. additionwas added to the solution in an argon gas atmosphere
  2. additionwas then added to the reaction system
  3. temperaturethe temperature thereof was raised up to 55° C
  4. customThe Pd/C catalyst was removed through filtration under reduced pressure
  5. washthe catalyst was washed with 25 mL of methanol
  6. temperaturethe resulting filtrate and the wash liquid were maintained at a temperature of 40° C
  7. additionWater (31 mL) was dropwise added
  8. customthereto thus separate out solid
  9. stirringthe resulting slurry was stirred at 10° C. overnight
  10. customThe resulting solid was separated from the slurry through filtration under reduced pressure
  11. washwashed with 7 mL of water
  12. customdried under reduced pressure at 70° C. for 5 hours

Sources & evidence

ORD record
ord-af374356c08043fca784c60682369f9b
Source dataset
uspto-grants-2011_11
Patent number
US08058432B2

Reaction notes

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