Water → Ethyl 6-chloro-5-methyl-4-(methylamino)nicotinate

HRID 2404047노트

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HRID 2404047 반응식
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[C:3]=1[CH3:14].[CH3:15][NH2:16].O>C(#N)C>[Cl:13][C:4]1[C:3]([CH3:14])=[C:2]([NH:16][CH3:15])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 6329MethylamineHCID 10752136Ethyl 4,6-dichloro-5-methylnicotinate

생성물 1

HCID 86713588Ethyl 6-chloro-5-methyl-4-(methylamino)nicotinate수율 81%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of ethyl 4,6-dichloro-5-methylnicotinate (2.6 g, 11.1 mmol) in acetonitrile (60 mL) was added dropwise 40% methylamine in water (689 mg, 22.2 mmol, 60 mL), and the mixture was stirred at 50° C. for 72 h. LCMS monitored the reaction was completed. The reaction mixture was concentrated and extracted with ethyl acetate (100 mL). The organic layer was separated, combined, washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column (petroleum ether:ethyl acetate=2:1) to get the title compound (2.05 g, 81%) as a colorless oil. MS (ES+) C10H13ClN2O2 requires: 228, 230. found: 229, 231 [M+H]+.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate (100 mL)
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column (petroleum ether:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-04df030245af4a17b9dee504bd3585fa
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802697B2

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