Ethyl isonicotinate → HCID 178419876, compound

HRID 1077043Notes

Reaction equation

HRID 1077043 reaction equation
[C:1]1([NH:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13](OCC)(=O)[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1>C(O)(C)C>[N:17]1[CH:18]=[CH:19][C:14]([C:13]2[NH:12][N:11]=[C:1]3[C:10]4[C:5]([CH:4]=[CH:3][C:2]=23)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 15291Ethyl isonicotinateHCID 75240Hydrazine, 1-naphthalenyl-

Product 1

HCID 178419876HCID 178419876, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 16 grams (0.10 mole) of 1-naphthyl hydrazine, 15.1 grams (0.10 moles) of ethyl isonicotinate and 300 ml. of isopropanol are stirred and refluxed for 48 hours. The solvent is removed in vacuo and the resultant 2-(1-naphthyl)-isonicotinic acid hydrazide is added to 125 ml. of phosphorous oxychloride and stirred and refluxed for about 15 hours. The reaction mixture is then concentrated in vacuo and the resultant simi-solid dissolved in about 250 ml. methylene dichloride. The methylene dichloride layer is washed with 100 ml of cold 2N potassium hydroxide, 100 ml. of water, dried with magnesium sulfate, filtered and concentrated in vacuo. Crystallization from ethanol/ether yields 3-(4-pyridyl)-2H-naphtho[1,2-c]pyrazole, m.p. 271°-273°.

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe solvent is removed in vacuo
  3. additionthe resultant 2-(1-naphthyl)-isonicotinic acid hydrazide is added to 125 ml
  4. temperaturerefluxed for about 15 hours
  5. concentrationThe reaction mixture is then concentrated in vacuo
  6. dissolutionthe resultant simi-solid dissolved in about 250 ml
  7. washThe methylene dichloride layer is washed with 100 ml of cold 2N potassium hydroxide, 100 ml
  8. dry with materialof water, dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customCrystallization from ethanol/ether

Sources & evidence

ORD record
ord-d09f5515a30045f3a497451eff3762ea
Source dataset
uspto-grants-1976_05
Patent number
US03959308

Reaction notes

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