Water → HCID 89421761, compound

HRID 1481781Notes

Reaction equation

HRID 1481781 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([O:6][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 105838872,4-Dichloronicotinic Acid

Product 1

HCID 89421761HCID 89421761, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dichloronicotinic acid (5.0 g, 26 mmol), benzyl bromide (3.7 mL, 31 mmol) and K2CO3 (7.2 g, 52 mmol) in DMF (50 mL) was stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic layers were combined and washed with water, brine, dried over sodium sulfate, evaporated and then purified by silica chromatography (0-7% ethyl acetate in hexanes) to give benzyl 2,4-dichloronicotinate (7.0 g, 96%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. custompurified by silica chromatography (0-7% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6b13ad5ad8af4b448186237d07f851ea
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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