Methanol → 4-Chloro-N-methylpicolinamide

HRID 387425

반응식

HRID 387425 반응식
Cl.C[O:3][C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][N:7]=1)=O.CO.[CH3:15][NH2:16]>O1CCCC1>[CH3:15][NH:16][C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][N:7]=1)=[O:3]

참가 물질

5

반응물 3

HCID 887MethanolHCID 6329MethylamineHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

생성물 1

HCID 14768144-Chloro-N-methylpicolinamide수율 80.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A suspension of 17.8 g (0.103 mol, 1 eq) of 4-chloro-pyridine-2-carboxylic acid methyl ester hydrochloride in 15 mL, of methanol was cooled to 0° C. and slowly treated with a 2.0 M solution of methylamine in tetrahydrofuran at a rate that kept internal temperature below 5° C. The reaction mixture was stirred at 0° C. for 2 hours, then slowly allowed to warm up to ambient temperature and stirred for 18 hours. Solvent was removed in vacuum, approx. 200 mL of ethyl acetate was added and the resulting suspension was filtered. The precipitate was washed with 100 mL of ethyl acetate. The combined ethyl acetate solutions were washed three times with 100 mL of brine and dried over sodium sulfate. Solvent was removed in vacuum to yield 14.16 g of the product as orange oil. Yield: 80.5%.

후처리

  1. customtemperature below 5° C
  2. temperatureto warm up to ambient temperature
  3. stirringstirred for 18 hours
  4. customSolvent was removed in vacuum, approx. 200 mL of ethyl acetate
  5. additionwas added
  6. filtrationthe resulting suspension was filtered
  7. washThe precipitate was washed with 100 mL of ethyl acetate
  8. washThe combined ethyl acetate solutions were washed three times with 100 mL of brine
  9. dry with materialdried over sodium sulfate
  10. customSolvent was removed in vacuum

출처 및 근거

ORD 기록
ord-a4e4c8b5a6254c1f8b5c73c2e6f29149
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372971B2

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