Sodium Hydroxide → Ethyl 5-cyanonicotinate

HRID 2241098Notes

Reaction equation

HRID 2241098 reaction equation
O=[C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4]N1S(C1C=CC=CC=1)(=O)=O.O=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C([O-])(=O)C.[NH4+].[OH-].[Na+]>C(O)C>[C:8]([C:5]1[CH:6]=[N:7][CH:2]=[C:20]([CH:4]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:9]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 70211Ethyl oxoacetateHCID 517165Ammonium AcetateHCID 23083348HCID 23083348, compound

Product 1

HCID 359390Ethyl 5-cyanonicotinateYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

31.4 g (120 mmol) of 2-oxo-1-(phenylsulfonyl)-1,2-dihydropyrimidine-5-carbonitrile and 10.2 g (100 mmol) of ethyl oxo-acetate were dissolved in 250 ml of ethanol, and allowed to undergo the reaction at 70° C. for 2 hours. 30.4 g (400 mmol) of ammonium acetate was added to the reaction solution to carry out the reaction at 90° C. for 4 hours. After completion of the reaction, this was cooled to room temperature, neutralized with 100 g (600 mmol) of 25% sodium hydroxide aqueous solution and then extracted twice with 40 ml of toluene. By concentrating the organic layer, 12.1 g (yield 68.7%) of the title compound was obtained (purity 98.2%, melting point 58-59° C.)

Workup

  1. customthe reaction at 70° C. for 2 hours
  2. customthe reaction at 90° C. for 4 hours
  3. customAfter completion of the reaction
  4. extractionextracted twice with 40 ml of toluene
  5. concentrationBy concentrating the organic layer

Sources & evidence

ORD record
ord-1ecf1e92e9fa4a99995aded52fc64e53
Source dataset
uspto-grants-2010_05
Patent number
US07723522B2

Reaction notes

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