Bistrimethylsilylacetamid → 1,4-Dihydro-5-hydroxy-4-oxo-N-(2-oxo-1-imidazolidinyl)-2-pyridinecarboxamide

HRID 1252594Notes

Reaction equation

HRID 1252594 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][N:19]2[CH2:23][CH2:22][NH:21][C:20]2=[O:24])=[O:17])=[CH:3]1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C>C(#N)C>[OH:8][C:7]1[C:2](=[O:1])[CH:3]=[C:4]([C:16]([NH:18][N:19]2[CH2:23][CH2:22][NH:21][C:20]2=[O:24])=[O:17])[NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11708267BistrimethylsilylacetamidHCID 141824551,4-dihydro-4-oxo-N-(2-oxo-1-imidazolidinyl)-5-(phenylmethoxy)-2-pyridinecarboxamide

Product 1

HCID 141824561,4-Dihydro-5-hydroxy-4-oxo-N-(2-oxo-1-imidazolidinyl)-2-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 12 g (0.0365 mol) of 1,4-dihydro-4-oxo-N-(2-oxo-1-imidazolidinyl)-5-(phenylmethoxy)-2-pyridinecarboxamide in 150 ml of acetonitrile was added 36.1 ml (0.146 mol) of bis(trimethylsilyl)acetamide to form a slightly turbid solution. After filtration, 6 g of 10% palladium on charcoal was added and hydrogen was passed through the stirred reaction mixture. After hydrogenation for 60 minutes, the catalyst was filtered off and 15 ml of methanol and 2 ml of acetic acid were added. Stirring was continued overnight; the title compound crystallized out, yielding 6.6 g, melting point 270°-275° C.

Workup

  1. customto form a slightly turbid solution
  2. filtrationAfter filtration, 6 g of 10% palladium on charcoal
  3. additionwas added
  4. customhydrogen was passed through the stirred reaction mixture
  5. filtrationthe catalyst was filtered off
  6. addition15 ml of methanol and 2 ml of acetic acid were added
  7. waitwas continued overnight
  8. customthe title compound crystallized out
  9. customyielding 6.6 g, melting point 270°-275° C.

Sources & evidence

ORD record
ord-cf5e420e94da4c93b5d6efc073995651
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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