5-Nitro-6-(2-methoxy-4-benzyloxy-benzoylamino)-2-pyridone → HCID 178493420, compound

HRID 35202Notes

Reaction equation

HRID 35202 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:29])[NH:8][C:9]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18]CC2C=CC=CC=2)=[CH:14][C:13]=1[O:26][CH3:27])([O-])=O>C(O)(=O)C.[Pd]>[CH3:27][O:26][C:13]1[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:12]=1[C:11]1[N:10]=[C:9]2[NH:8][C:7](=[O:29])[CH2:6][CH:5]=[C:4]2[N:1]=1

Participants

4

Reactant 1

HCID 212958065-Nitro-6-(2-methoxy-4-benzyloxy-benzoylamino)-2-pyridone

Product 1

HCID 178493420HCID 178493420, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

3.95 g of 5-nitro-6-(2-methoxy-4-benzyloxy-benzoylamino)-2-pyridone were hydrogenated in 350 ml of glacial acetic acid after the addition of 1 g of 10% palladium-on-charcoal for 1.7 hours at 80° C. under a pressure of 5 bar. The reaction mixture was then stirred at 100° C. for 1.3 hours. The catalyst was filtered off, and the filtrate was allowed to cool. The product which precipitated was washed with ether. By evaporating the filtrate and adding ether, further fractions were obtained. Yield: 2.3 g (60% of theory). Melting point: over 270° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. temperatureto cool
  3. customThe product which precipitated
  4. washwas washed with ether
  5. customBy evaporating the filtrate
  6. additionadding ether
  7. customfurther fractions were obtained
  8. customover 270° C.

Sources & evidence

ORD record
ord-b5abdcdb5c4d4ab6ad43c01a3940bcc1
Source dataset
uspto-grants-1988_08
Patent number
US04766130

Reaction notes

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