Water → HCID 59318347, compound

HRID 423304Notes

Reaction equation

HRID 423304 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Cl:11])[C:8](Cl)=[N:7][CH:6]=1)[CH3:2].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[Cu]>[Cl:11][C:9]1[CH:10]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:13])[CH:6]=[N:7][C:8]=1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268Pyrrolidine2×HCID 16762519Ethyl 5,6-Dichloronicotinate

Product 1

HCID 59318347HCID 59318347, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5,6-dichloronicotinic acid ethyl ester (1.00 g, 4.57 mmol), pyrrolidine (325 mg, 4.57 mmol), potassium carbonate (632 mg, 4.57 mmol) and copper powder (34 mg) in DMF (6.8 mL) was heated at 130° C. in the microwave for 20 min. Further pyrrolidine (163 mg, 2.29 mmol) was added and the reaction heated at 130° C. for 20 min. Water (7 mL) was added and the mixture extracted with ethyl acetate (2×14 mL). The combined organic extracts were washed with water (7 mL) and brine (7 mL) before being dried (phase separator) and concentrated in vacuo to give the title compound as an orange oil (1.06 g, 4.17 mmol). δH (methanol-d4, 400 MHz): 8.45 (1H, d), 7.98 (1H, d), 4.31 (2H, q), 3.82-3.75 (4H, m), 2.0-1.93 (4H, m), 1.36 (3H, t) ppm. MS (ES): C12H15ClN2O2 requires 254, 256; found 255, 257 (MH+).

Workup

  1. temperaturethe reaction heated at 130° C. for 20 min
  2. extractionthe mixture extracted with ethyl acetate (2×14 mL)
  3. washThe combined organic extracts were washed with water (7 mL) and brine (7 mL)
  4. custombefore being dried (phase separator)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3e9c80a8b9c4965acb93a0ed142566e
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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