Hydrazine hydrate (1:1) → HCID 12297944, compound

HRID 1730643Notes

Reaction equation

HRID 1730643 reaction equation
[NH2:1][C:2]1[N:12]=[C:11]([CH3:13])[C:10]([NH:14][C:15](=[O:17])[CH3:16])=[C:9]([CH3:18])[C:3]=1[C:4](OCC)=[O:5].O.[NH2:20][NH2:21]>O.CO>[NH2:1][C:2]1[N:12]=[C:11]([CH3:13])[C:10]([NH:14][C:15](=[O:17])[CH3:16])=[C:9]([CH3:18])[C:3]=1[C:4]([NH:20][NH2:21])=[O:5]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12297943HCID 12297943, compound

Product 1

HCID 12297944HCID 12297944, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-amino-5-acetamido-4,6-dimethylnicotinate (45.3 g., 0.18 mole) and hydrazine hydrate (100 ml.) is heated in an oil bath with stirring at 120° C. for two hours. The mixture is cooled, the solid collected, and a second crop of solid obtained by evaporating the mother liquor to about half its initial volume. The combined solids melt at 293° C. (dec.), yield 38.1 g. (89%). Analytically pure compound is obtained by dissolving the solid in about six and one-half parts (volume by weight) of hot water and diluting the filtered solution with methanol. The purified product decomposed at about 309° C. with only partial melting.

Workup

  1. temperatureis heated in an oil bath
  2. temperatureThe mixture is cooled
  3. customthe solid collected
  4. customa second crop of solid obtained
  5. customby evaporating the mother liquor to about half its initial volume
  6. customAnalytically pure compound is obtained
  7. customdecomposed at about 309° C. with only partial melting

Sources & evidence

ORD record
ord-61250c22e6cd452f97f736c68fb8666a
Source dataset
uspto-grants-1976_11
Patent number
US03993656

Reaction notes

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