Hydrazine hydrate (1:1) → 5-(Benzyloxy)-2-(hydrazinocarbonyl)-4-oxo-1,4-dihydropyridine

HRID 1249600Notes

Reaction equation

HRID 1249600 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:20])[CH:11]=[C:12]([C:15](OCC)=[O:16])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:22][NH2:23]>>[CH2:1]([O:8][C:9]1[C:10](=[O:20])[CH:11]=[C:12]([C:15]([NH:22][NH2:23])=[O:16])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 867411755-(Benzyloxy)-1,4-dihydro-4-oxo-2-pyridinecarboxylic acid, ethyl ester

Product 1

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

Procedure

A suspension of 5-(benzyloxy)-1,4-dihydro-4-oxo-2-pyridinecarboxylic acid, ethyl ester (7.1 g, 26 mmole) in 99% hydrazine hydrate (15 ml) was heated until most of the solid dissolved. The resulting mixture was stirred for 25 minutes at ambient temperature, the excess hydrazine was removed under high vacuum and the solid residue was treated with methanol. The volatiles were removed in vacuo (repeat methanol treatment and evaporation twice), the solid residue was washed with methanol, hexane, and dried to afford 6 g of the title compound.

Workup

  1. temperaturewas heated until most of the solid
  2. dissolutiondissolved
  3. customthe excess hydrazine was removed under high vacuum
  4. additionthe solid residue was treated with methanol
  5. customThe volatiles were removed in vacuo (
  6. custommethanol treatment and evaporation twice), the solid residue
  7. washwas washed with methanol, hexane
  8. customdried

Sources & evidence

ORD record
ord-8f078f409c894c199c19e22035ae4e2a
Source dataset
uspto-grants-1986_12
Patent number
US04632985

Reaction notes

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