HCID 19770728, compound → HCID 19770729, compound

HRID 1681113Notes

Reaction equation

HRID 1681113 reaction equation
[N+:1]([C:4]1[C:5](=[O:21])[NH:6][C:7]([CH2:12][O:13]CC2C=CC=CC=2)=[C:8]([CH2:10][CH3:11])[CH:9]=1)([O-])=O>O1CCCC1.CO.[Pd]>[NH2:1][C:4]1[C:5](=[O:21])[NH:6][C:7]([CH2:12][OH:13])=[C:8]([CH2:10][CH3:11])[CH:9]=1

Participants

5

Reactant 1

HCID 19770728HCID 19770728, compound

Product 1

HCID 19770729HCID 19770729, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-nitro-5-ethyl-6-benzyloxymethyl-2(1H)-pyridinone (576 mg, 2.0 mmol) in tetrahydrofuran (15 mL) and methanol (15 mL) containing 10% palladium/charcoal (130 mg) was hydrogenated at atomspheric pressure, monitoring the progress by thin layer chromatography (tlc). Additional catalyst was added in 100 mg portions after day 2 and day 3. After 3-4 days, the catalyst was filtered and the solvents evaporated. The catalyst was vigorously washed with methanol/chloroform and combined solvents evaporated. The residue was triturated with methylene chloride and productcollected by filtration to give 136 mg of 90% pure product. This material was used without further purfification.

Workup

  1. additionAdditional catalyst was added in 100 mg portions after day 2 and day 3
  2. filtrationthe catalyst was filtered
  3. customthe solvents evaporated
  4. washThe catalyst was vigorously washed with methanol/chloroform
  5. customevaporated
  6. customThe residue was triturated with methylene chloride
  7. filtrationproductcollected by filtration

Sources & evidence

ORD record
ord-7a15f18a3cc049298b82ecbc8ac052bb
Source dataset
uspto-grants-1992_12
Patent number
US05169769

Reaction notes

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