Hydrazine hydrate (1:1) → HCID 12246613, compound

HRID 1604899Notes

Reaction equation

HRID 1604899 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:25])=[N:8][C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:10][C:11]=1[C:12](OCC)=[O:13])=O)C.O.[NH2:27][NH2:28]>>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:9]2[N:8]=[C:7]([CH3:25])[C:6]3[C:4](=[O:3])[NH:27][NH:28][C:12](=[O:13])[C:11]=3[CH:10]=2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12246600HCID 12246600, compound

Product 1

HCID 12246613HCID 12246613, compound

Procedure

10 parts by weight of 3,4-diethoxycarbonyl-6-(p-methoxyphenyl)-2-methylpyridine is incorporated into 40 parts by volume of hydrazine hydrate, and the resulting mixture is refluxed for three hours. The precipitated crystals are collected by filtration, washed with ethanol and suspended in 100 parts by volume of water. The mixture is acidified by the addition of acetic acid to obtain 1,2,3,4 -tetrahydro-7-(p-methoxyphenyl)- 5-methyl-1,4-dioxopyrido[3,4-d]pyridazine as colorless fine crystals. A mixture is made of 3.0 parts by weight of the fine crystals, 45 parts by volume of phosphorus oxychloride and 4.5 parts by volume of N,N-dimethylaniline. The mixture is heated at temperature ranging from 90° to 100°C for three hours. Then, the reaction mixture is left standing at room temperature overnight. The precipitated crystals are collected by filtration, washed with ether, recrystallized from chloroform to obtain the desired compounds melting at 214° to 219°C (decomposition) as pale yellow needles.

Workup

  1. temperaturethe resulting mixture is refluxed for three hours
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed with ethanol
  4. additionThe mixture is acidified by the addition of acetic acid

Sources & evidence

ORD record
ord-932c2d2d983c47b9b0ae9241df10fb3b
Source dataset
uspto-grants-1976_04
Patent number
US03948908

Reaction notes

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