Methyl iodide → Methyl 3-chloroisonicotinate

HRID 1873991

반응식

HRID 1873991 반응식
[C:1](=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:16]=[N:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].CI>CS(C)=O>[Cl:7][C:8]1[CH:16]=[N:15][CH:14]=[CH:13][C:9]=1[C:10]([O:12][CH3:1])=[O:11]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27358163-Chloropyridine-4-carboxylic acid

생성물 1

HCID 15324397Methyl 3-chloroisonicotinate수율 56%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Potassium carbonate (36.3 g, 263 mmol) was added to 3-chloroisonicotinic acid (10.35 g, 65.7 mmol) in DMSO (50 mL). After 30 min, MeI (8.22 mL, 131 mmol) was added. The mixture was stirred at room temperature for 2 h, quenched with saturated NH4Cl (300 mL) and water (200 mL), and extracted with EtOAc (3×200 mL). The combined extracts were washed with brine (2×50 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 10-30% ethyl acetate in hexanes, gave methyl 3-chloroisonicotinate as a colorless liquid (6.275 g, 56% yield). MS (ES+) m/z: 172 (M+H); LC retention time: 2.45 min (analytical HPLC Method A).

후처리

  1. customquenched with saturated NH4Cl (300 mL) and water (200 mL)
  2. extractionextracted with EtOAc (3×200 mL)
  3. washThe combined extracts were washed with brine (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washSilica gel chromatography, eluting with 10-30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-9804765ee1dc41b4b56017fcd5343ca9
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304539B2

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