Methyl iodide → 1,2,3,4-Tetrahydro-1-methylquinoline

HRID 641916

反応式

HRID 641916 の反応式
[H-].[Na+].[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.I[CH3:14]>O1CCCC1>[CH3:14][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 694601,2,3,4-Tetrahydroquinoline

生成物 1

HCID 681091,2,3,4-Tetrahydro-1-methylquinoline収率 64.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
2.5 °C

実験手順

NaH (12 g, 60%, 300.00 mmol) was added in several batches, to a solution of 1,2,3,4-tetrahydroquinoline (26.6 g, 199.70 mmol) in tetrahydrofuran (150 mL) at 0-5° C. The resulting solution was maintained at 0-5° C. for 30 minutes, then iodomethane (50 g, 352.11 mmol) was added dropwise (at 0-5° C.). The resulting solution was then stirred at room temperature overnight. The mixture was filtered, and the filtrate was purified by column chromatography using a 1:100 ethyl acetate/petroleum ether solvent system to afford 19 g (61%) of 1-methyl-1,2,3,4-tetrahydroquinoline as a yellow liquid.

後処理

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified by column chromatography

出典と根拠

ORDレコード
ord-d054ad27cc39446d909b8aae5977ee47
出典データセット
uspto-grants-2010_04
特許番号
US07696229B2

関連ノート

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