Sodium Acetate → 2-(Acetoxymethyl)-6-chloroisonicotinic acid

HRID 623631노트

반응식

HRID 623631 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([Cl:13])[N:12]=1)[C:6]([O:8]C)=[O:7].[C:14]([O-:17])(=[O:16])[CH3:15].[Na+]>CN(C)C(=O)C.O>[C:14]([O:17][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([Cl:13])[N:12]=1)[C:6]([OH:8])=[O:7])(=[O:16])[CH3:15]

참가 물질

5

반응물 2

HCID 517045Sodium AcetateHCID 86225002Methyl 2-(bromomethyl)-6-chloropyridine-4-carboxylate

생성물 1

HCID 874269902-(Acetoxymethyl)-6-chloroisonicotinic acid

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

반응 조건

온도
120 °C

실험 절차

A mixture of methyl 2-(bromomethyl)-6-chloroisonicotinate and sodium acetate in N,N-dimethylacetamide is stirred at 120° C. for 2 hours. The mixture is cooled to room temperature and diluted with water (50 mL). The mixture is washed with ethyl acetate/toluene (2:1, 80 mL×2). Water layer is acidified (to pH 4) by the addition of 2M hydrochloric acid, extracted with ethyl acetate (80 mL×2), dried over sodium sulfate. The organic solvent is removed under reduced pressure to give the title compound as a crude product (590 mg, clear brown oil, include N,N-dimethylacetamide). This is used without purification in the next step.

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. washThe mixture is washed with ethyl acetate/toluene (2:1, 80 mL×2)
  3. additionby the addition of 2M hydrochloric acid
  4. extractionextracted with ethyl acetate (80 mL×2)
  5. dry with materialdried over sodium sulfate
  6. customThe organic solvent is removed under reduced pressure

출처 및 근거

ORD 기록
ord-b812e295a2e94b0e99db15c15cb13005
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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