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

HRID 2274208ノート

反応式

HRID 2274208 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-64c87db8c81c4be48c61d85a601d2dc7
出典データセット
uspto-grants-2015_09
特許番号
US09126951B2

反応ノート

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