Ethyl bromoacetate → (Ethoxycarbonyl)-methyl 2-cyanonicotinate

HRID 232014Notes

Reaction equation

HRID 232014 reaction equation
[C:1]([C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O-:7])=[O:6])#[N:2].[K+].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].COCCOCCN(CCOCCOC)CCOCCOC>C1(C)C=CC=CC=1>[C:1]([C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 23690323Potassium 2-cyanonicotinate

Product 1

HCID 14050326(Ethoxycarbonyl)-methyl 2-cyanonicotinateYield 100.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (40 cc) containing compound 3 (4.1 g; 0.022 mol), ethyl bromoacetate (3.35 g; 0.02 mol) and TDA-1 (0.3 cc) is heated under reflux for 4 hours. The toluene is then evaporated off and the residue taken up with water and then extracted with dichloromethane. After drying, evaporating and crystallization in pentane, (ethoxycarbonyl)-methyl 2-cyanonicotinate (4.7 g; m.p. 74° C.) is obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. customThe toluene is then evaporated off
  4. extractionextracted with dichloromethane
  5. customAfter drying
  6. customevaporating
  7. customcrystallization in pentane

Sources & evidence

ORD record
ord-08e313408e5e4fafa6beed1a00e4b047
Source dataset
uspto-grants-1989_07
Patent number
US04851396

Reaction notes

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