HCID 22929892, compound → HCID 178485230, compound

HRID 1295938Notes

Reaction equation

HRID 1295938 reaction equation
[CH3:1][NH:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[C:7]([CH2:12][N:13]=[N+]=[N-])=[CH:6][C:5]=1[N:16]([CH3:18])[CH3:17]>CO.[C].[Pd]>[CH3:1][NH:2][C:3]([C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][C:5]=1[N:16]([CH3:18])[CH3:17])[CH2:12][NH:13][C:10]2=[NH:11])=[O:19]

Participants

4

Reactant 1

HCID 22929892HCID 22929892, compound

Product 1

HCID 178485230HCID 178485230, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

After dissolving N1-methyl-4-(azidomethyl)-5-cyano-2-(dimethylamino)benzamide (755 mg, 2.9 mmol) in methanol (50 ml), 10% palladium-carbon (50% wet) (0.2 g) was added prior to catalytic reduction for 30 minutes at room temperature and normal pressure. The catalyst was separated off, the solvent was distilled off under reduced pressure and ethyl acetate was added to the residue for crystallization. This was filtered off to yield the title compound (283 mg) as a faint yellow powder. (42% yield)

Workup

  1. additionwas added
  2. customThe catalyst was separated off
  3. distillationthe solvent was distilled off under reduced pressure and ethyl acetate
  4. additionwas added to the residue for crystallization
  5. filtrationThis was filtered off

Sources & evidence

ORD record
ord-f063f03be0a34c0ba663e9c31246b2f0
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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