2-Hydrazinylpyrimidine → HCID 178515198, compound

HRID 1248449Notes

Reaction equation

HRID 1248449 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=O.[NH:18]([C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[NH2:19]>C(O)C>[F:12][C:9]1[CH:8]=[CH:7][C:6]2[NH:5][CH:4]=[C:3]3[C:13](=[O:15])[N:18]([C:20]4[N:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[N:19]=[C:2]3[C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 3465582-HydrazinylpyrimidineHCID 1479088Ethyl 4-chloro-6-fluoroquinoline-3-carboxylate

Product 1

HCID 178515198HCID 178515198, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.0 of ethyl 4-chloro-6-fluoroquinolin-3-carboxylate and 0.95 g of 2-hydrazinopyrimidine in 40 ml of 95% ethanol is heated under reflux for 16 hours. The reaction mixture is filtered and the resulting solid is taken up in 20 ml of N sodium hydroxide and sufficient water to effect solution. Ammonium chloride (10.7 g) is added, the resulting precipitate is collected, washed with water and dried to yield 8-fluoro-2-(2-pyrimidyl)-pyrazolo[4,3-c]quinolin-3(5H)-one, as a hydrate, m.p. above 350°; IR (KBr) 800, 829, 870, 880 cm-1.

Workup

  1. temperatureunder reflux for 16 hours
  2. filtrationThe reaction mixture is filtered
  3. additionAmmonium chloride (10.7 g) is added
  4. customthe resulting precipitate is collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ce2b3867f51247be8640151e76e5d618
Source dataset
uspto-grants-1985_06
Patent number
US04524146

Reaction notes

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