Acetohydrazide → HCID 12335462, compound

HRID 1701701Notes

Reaction equation

HRID 1701701 reaction equation
[CH:1]([C:3]1[N:12]=[C:11]2[C:6]([C:7](=[O:16])[C:8]([C:13]([OH:15])=[O:14])=[CH:9][NH:10]2)=[CH:5][CH:4]=1)=[O:2].[C:17](NN)(=O)[CH3:18]>C(O)C>[CH2:17]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([CH:1]=[O:2])[N:12]=2)[C:7](=[O:16])[C:8]([C:13]([OH:15])=[O:14])=[CH:9]1)[CH3:18]

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 53759149HCID 53759149, compound

Product 1

HCID 12335462HCID 12335462, compoundYield 118%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 2 g of 7-formyl-3-carboxy-4-oxo-1, 4-dihydro-1,8-naphthyridine and 0.51 g of acethydrazide and 20 ml of ethanol are stirred and refluxed for 11/2 hours. The mixture was cooled and the solids were filtered and washed with a little ethanol and dried at room temperature. Several washings with hot cellosolve and dimethyl formamide yielded 2 g of 1-ethyl-3-carboxy-4-oxo-1, 4 dihydro-1,8 naphthyridine-7 carboxaldehyde acethydrazone m.p. 300°.

Workup

  1. temperaturerefluxed for 11/2 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe solids were filtered
  4. washwashed with a little ethanol
  5. customdried at room temperature
  6. washSeveral washings with hot cellosolve and dimethyl formamide

Sources & evidence

ORD record
ord-6458e8a2214e49efa423c64dfd97290d
Source dataset
uspto-grants-1980_03
Patent number
US04195087

Reaction notes

Loading…