Trifluoroacetate → 1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinecarboxylic acid, hydrazide

HRID 1252598Notes

Reaction equation

HRID 1252598 reaction equation
[O:1]=[C:2]1[C:7]([O:8]CC2C=CC=CC=2)=[CH:6][NH:5][C:4]([C:16]([NH:18][NH2:19])=[O:17])=[CH:3]1.FC(F)(F)C([O-])=O>C(#N)C>[OH:8][C:7]1[C:2](=[O:1])[CH:3]=[C:4]([C:16]([NH:18][NH2:19])=[O:17])[NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 84468TrifluoroacetateHCID 141824695-(Benzyloxy)-2-(hydrazinocarbonyl)-4-oxo-1,4-dihydropyridine

Product 1

HCID 141824671,4-Dihydro-5-hydroxy-4-oxo-2-pyridinecarboxylic acid, hydrazide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, hydrazide, trifluoroacetate (1:2) salt was dissolved in 250 ml of acetonitrile and stirred with cooling for 1 hour. The crystals were then filtered off and resuspended in 600 ml of acetonitrile. Bis(trimethylsilyl)acetamide (135 ml) was added followed by 28 g of 10% palladium on charcoal. Then hydrogen was passed through the stirred solution. The hydrogenation was complete after 90 minutes. After filtration, 70 ml of methanol and 2 ml of acetic acid were added. After stirring overnight, the crystals formed were filtered off, yielding 19.4 g of the title compound, melting point 290°-340° C., dec.

Workup

  1. temperaturewith cooling for 1 hour
  2. filtrationThe crystals were then filtered off
  3. additionBis(trimethylsilyl)acetamide (135 ml) was added
  4. filtrationAfter filtration, 70 ml of methanol and 2 ml of acetic acid
  5. additionwere added
  6. stirringAfter stirring overnight
  7. customthe crystals formed
  8. filtrationwere filtered off

Sources & evidence

ORD record
ord-9025f366572b4c8c8a419dab4bbd02c4
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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