Benzyl Alcohol → HCID 70653970, compound

HRID 336512Notes

Reaction equation

HRID 336512 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9](Cl)[N:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H][H]>O.CN(C)C=O>[CH2:14]([O:21][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=1)[C:5]([OH:7])=[O:6])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 948302,6-Dichloroisonicotinic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 70653970HCID 70653970, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In an argon atmosphere, 2,6-dichloroisonicotinic acid (57.6 g) was gradually added to 55% sodium hydride (52.5 g) and dimethylformamide (1 L) while being cooled and stirred. Subsequently, benzyl alcohol (93 mL) was gradually added dropwise to the reaction product at the same temperature. After hydrogen was no longer generated, the reaction product was stirred for 4 hours at 80° C., and water (1 L) was then added thereto. The mixture was separated by a mixed solvent (1 L) of ethyl acetate and n-hexane (1:1). The acidity of the aqueous layer was lowered with acetic acid (75.5 mL), and water (1.7 L) was further added thereto. The precipitate was filtered and dried to obtain Compound 2a.

Workup

  1. temperaturewhile being cooled
  2. stirringthe reaction product was stirred for 4 hours at 80° C.
  3. customThe mixture was separated by a mixed solvent (1 L) of ethyl acetate and n-hexane (1:1)
  4. additionwas further added
  5. filtrationThe precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-538b8bd398b14de7bb79a705935706e1
Source dataset
uspto-grants-2014_11
Patent number
US08889699B2

Reaction notes

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