Water → HCID 15123266, compound

HRID 520478Notes

Reaction equation

HRID 520478 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][C:9]1[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.O>CN(C=O)C>[N:19]1([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 53404482Methyl 6-(chloromethyl)pyridine-2-carboxylate

Product 1

HCID 15123266HCID 15123266, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

K2CO3 (66 g, 0.48 mol) was added to a solution of methyl 6-(chloromethyl)picolinate 67 (45.0 g) and pyrrolidine 68 (34 g, 0.48 mol) in DMF (300 mL). The reaction mixture was heated at 80° C. for 12 h. H2O (300 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to give 69 (36 g).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-534ca0af16bb497b946d9c0a2804877b
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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