2-Hydrazinopyridine → HCID 14986969, compound

HRID 727782Notes

Reaction equation

HRID 727782 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH:8]([CH2:14][C:15]([OH:17])=O)[CH2:7][CH2:6]2.[NH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[NH2:19]>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9]3[CH:8]([CH2:14][C:15](=[O:17])[N:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[N:19]=3)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 13574088(6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid

Product 1

HCID 14986969HCID 14986969, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 20 g of 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-acetic acid, 10.9 g of 2-hydrazinopyridine and 150 ml of ethanol is heated under reflux for 2 hours. The resulting crystals are collected, whereto 50 ml of acetic acid is added. The mixture is heated under reflux for 30 minutes. Acetic acid is distilled off under reduced pressure, and water is added to the residue. The resultant crystals are collected and recrystallized from chloroform - ethanol to give 21.5 g of 8-methoxy-2-(2-pyridyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one as white crystals, m.p. 194°-196° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. customThe resulting crystals are collected
  4. additionwhereto 50 ml of acetic acid is added
  5. temperatureThe mixture is heated
  6. temperatureunder reflux for 30 minutes
  7. distillationAcetic acid is distilled off under reduced pressure, and water
  8. additionis added to the residue
  9. customThe resultant crystals are collected
  10. customrecrystallized from chloroform - ethanol

Sources & evidence

ORD record
ord-3cc91d8db86e437e969845aa1f00c4d0
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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