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

HRID 929997

반응식

HRID 929997 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-62e4d1b332844826bfe32f1ac5a90df1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296722B2

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