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N-Methylethylamine → 6-Chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester

HRID 1753881
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HRID 1753881 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([Cl:13])=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].[CH3:15][NH:16][CH2:17][CH3:18].CCN(C(C)C)C(C)C.[OH-].[Na+]>CN1C(=O)CCC1.O.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:16]([CH2:17][CH3:18])[CH3:15])=[N:8][C:9]([Cl:13])=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]
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참가 물질

8

반응물 4

HCID 12219N-MethylethylamineHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 70700301Ethyl 2,6-dichloro-4-methylnicotinate

생성물 1

HCID 866643246-Chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester수율 44.6%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8857Ethyl Acetate용매
HCID 13387N-methyl-2-pyrrolidone용매

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온도
90 °C

실험 절차

A mixture of 8.2 g (35.0 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid ethylester, 3.7 ml (43.8 mmol) N-methylethylamine and 8.9 ml (52.5 mmol) DIPEA in NMP (25 ml) was heated in the MW to 90° C. for 1 h. Then the solution was diluted with water, a 1M aq. NaOH sol. and EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 4.0 g (15.6 mmol, 44%) 6-chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester.

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by CC (hexane/EtOAc 9:1)

출처 및 근거

ORD 기록
ord-8c9f46a5599546d8aacfa2eb5b9190e3
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09168259B2

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