Hydrazine hydrate (1:1) → HCID 11544453, compound

HRID 1357468Notes

Reaction equation

HRID 1357468 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:6][C:5]=1[C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O.[NH2:28][NH2:29]>C(O)C>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]2[C:3](=[O:2])[NH:29][N:28]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]=2[N:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67483868HCID 67483868, compound

Product 1

HCID 11544453HCID 11544453, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Benzoyl-6-benzyloxynicotinic acid methyl ester (1.14 g) and hydrazine monohydrate (0.40 ml) were stirred together in ethanol (50 ml) at reflux overnight. The reaction was cooled (ice bath) precipitating a solid, which was separated by filtration and washed with diethyl ether. This was 2-benzyloxy-8-phenyl-6H-pyrido[2,3-d]pridazin-5-one (0.845 g). 1H NMR (400 MHz, DMSO) δ5.42 (2H, s), 7.33 (6H, m), 7.50 (3H, m), 7.86 (2H, m), 8.51 (1H, d, J=9.7 Hz), 13.04 (1H, s); MS (ES+) m/e 330 [MH]+.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe reaction was cooled (ice bath)
  3. customprecipitating a solid, which
  4. customwas separated by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-731453b62663411290e247a7afb0fbf0
Source dataset
uspto-grants-2003_07
Patent number
US06593325B1

Reaction notes

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