Acetic Anhydride → N-[1-(6-Chloro-2-pyridyl)-2-pyrazolin-3-yl]formamide

HRID 67904Notes

Reaction equation

HRID 67904 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([NH:13][C:14](=[O:16])C)=[N:9]2)[CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C>C(O)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([NH:13][CH:14]=[O:16])=[N:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13050983N-[1-(6-Chloro-2-pyridyl)-2-pyrazolin-3-yl]acetamide

Product 1

HCID 13050984N-[1-(6-Chloro-2-pyridyl)-2-pyrazolin-3-yl]formamide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 5.0 g. of 2-(3-amino-2-pyrazolin-1-yl)-6-chloropyridine (prepared as described in Example 3) and 25 ml. of a mixture of formic acid and acetic anhydride (Feiser and Feiser, Reagents for Organic Synthesis, Vol. 1, page 4) at room temperature gives an immediate yellow precipitate. The precipitate is collected by filtration then is recrystallized from acetone-hexane to give 3.05 g. of the product of the Example as off-white crystals, m.p. 190°-192° C.

Workup

  1. additionA mixture of 5.0 g
  2. customgives an immediate yellow precipitate
  3. filtrationThe precipitate is collected by filtration
  4. customthen is recrystallized from acetone-hexane
  5. customto give 3.05 g

Sources & evidence

ORD record
ord-b3c9d641736e4e999de7ec8af81e9585
Source dataset
uspto-grants-1982_08
Patent number
US04347251

Reaction notes

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