HCID 58018333, compound → HCID 58018319, compound

HRID 557443Notes

Reaction equation

HRID 557443 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:20]([O-])=O)=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[NH2:20][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:9])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 58018333HCID 58018333, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58018319HCID 58018319, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To 80 mL of methanol, there were added 8.3 g of 5-(N-tert-butoxycarbonyl-N-methyl-aminomethyl)-2-nitrobenzoic acid prepared in the foregoing Step 2 and 500 mg of 10% Pd/C (wet product), then hydrogen gas was introduced into the resulting dispersion and the mixture was then stirred at room temperature. After 1.5 hours, additional 500 mg of 10% Pd/C was further added to the mixture and the latter was stirred over 7 hours in a hydrogen gas atmosphere. The catalyst was removed by the filtration through Celite and the Celite was washed with methanol. The filtrate was concentrated to dryness to thus give the title compound.

Workup

  1. customThe catalyst was removed by the filtration through Celite
  2. washthe Celite was washed with methanol
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-2facd191d5ec482bbf68e01361fe1cb1
Source dataset
uspto-grants-2011_11
Patent number
US08058432B2

Reaction notes

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