Ethyl Acetate → HCID 16783361, compound

HRID 1409724Notes

Reaction equation

HRID 1409724 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10]C)=[O:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.C(OCC)(=O)C>CN1CCCC1=O>[CH3:21][C:22]1[N:23]([C:2]2[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=2)[CH:24]=[CH:25][N:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 127492-Methylimidazole2×HCID 81531DiisopropylethylamineHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 16783361HCID 16783361, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 6-chloropyridine-3-carboxylate (0.75 g), N,N-diisopropyl-ethyl-amine (1.75 mL) and 2-methyl-1H-imidazole (0.58 g) in N-methylpyrrolidone (6 mL) is heated to 100° C. overnight. Additional 2-methyl-1H-imidazole (0.58 g) is added and the reaction continues at 100° C. for two days. Ethyl acetate is added and the mixture is washed with saturated ammonium chloride. The organic phase is dried over MgSO4 and concentrated in vacuo. The crude ester is dissolved in MeOH (4 mL) and KOH (1.5 g) in water (2 mL) is added and kept at room temperature for 2 h. The MeOH is removed in vacuo and the aqueous phase is acidified with 1N HCl and extracted with dichloromethane. The organic phase is dried over MgSO4 and concentrated to afford the title compound. LC (method 20): tR=0.51 min; Mass spectrum (APCI): m/z=204 [M+H]+.

Workup

  1. washthe mixture is washed with saturated ammonium chloride
  2. dry with materialThe organic phase is dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe crude ester is dissolved in MeOH (4 mL)
  5. additionKOH (1.5 g) in water (2 mL) is added
  6. waitkept at room temperature for 2 h
  7. customThe MeOH is removed in vacuo
  8. extractionextracted with dichloromethane
  9. dry with materialThe organic phase is dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f672bb42dae3448f8931f272b3a65e0e
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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