Diethylamine → Ethyl 6-((diethylamino)methyl)picolinate

HRID 929997

Reaction equation

HRID 929997 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=1.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:14]([N:16]([CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=1)[CH2:17][CH3:18])[CH3:15]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 15614003Ethyl 6-(chloromethyl)pyridine-2-carboxylate

Product 1

HCID 67125927Ethyl 6-((diethylamino)methyl)picolinateYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of ethyl 6-(chloromethyl)picolinate (200 mg, 1.00 mmol) and KI (166 mg, 1.00 mmol) in DMF was added N,N-diethyl amine (73 mg, 1.00 mmol) and K2CO3 (304 mg, 2.20 mmol). The reaction mixture was stirred at rt for 5 h. LC-MS indicated the presence of product. The solvent was evaporated under reduced pressure and the residue was partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was washed with water (15 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure to give ethyl 6-((diethylamino)methyl)picolinate (150 mg, 64%) as an oil. LC-MS (ESI) m/z 237 (M+H)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between EtOAc (20 mL) and water (20 mL)
  3. washThe organic layer was washed with water (15 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-62e4d1b332844826bfe32f1ac5a90df1
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Linked notes

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