Sodium Carbonate → HCID 69355460, compound

HRID 983410Notes

Reaction equation

HRID 983410 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13](F)[CH:12]=2)[CH:8]=[N:7][CH:6]=1)[CH3:2].C([O-])(=[O:23])C.[K+].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[Na+].[Na+]>CC#N>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([OH:23])[CH:12]=2)[CH:8]=[N:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 69357950HCID 69357950, compound

Product 1

HCID 69355460HCID 69355460, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-(4-cyano-3-fluoro-phenyl)-nicotinic acid ethyl ester from Example 1a, potassium acetate (2 equiv.), and 18-crown-6 ether (2 equiv.) in MeCN is heated at reflux in 36 h. The mixture is cooled, aqueous sodium carbonate is added and stirred at room temperature overnight. The mixture was extracted with ether (discarded). The aqueous layer is neutralized with 1N HCl, extracted with EtOAc, dried over MgSO4, and concentrated. Purification by flash column chromatography gives 5-(4-cyano-3-hydroxy-phenyl)-nicotinic acid ethyl ester.

Workup

  1. temperatureis heated
  2. temperatureat reflux in 36 h
  3. temperatureThe mixture is cooled
  4. extractionThe mixture was extracted with ether (discarded)
  5. extractionextracted with EtOAc
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-64ad88f3e4ab4e33b10a215e3ed424f0
Source dataset
uspto-grants-2005_03
Patent number
US06864267B2

Reaction notes

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