Formaldehyde → 6-Methylnicotine, (A+-)-

HRID 1761

反応式

HRID 1761 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1.[CH2:13]=O.[OH-].[Na+]>C(O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([CH3:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 127496842-Methyl-5-(pyrrolidin-2-yl)pyridine

生成物 1

HCID 50207116-Methylnicotine, (A+-)-収率 92%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

Into a round bottom flask was placed XVI (2.0 g), and formaldehyde (37% w/v in water, 20 mL) and formic acid (95-97% w/v, 45 mL), both a 0° C., were added. The mixture then was refluxed under nitrogen for 8 hr. The cooled reaction mixture was basified with aqueous sodium hydroxide (50% w/v) to pH 8-9, and the solution extracted with chloroform (5×25 mL). The combined organic liquors were dried over anhydrous sodium sulfate, filtered and evaporated; and the resulting oil distilled under reduced pressure to afford XVII as a clear odorless oil (b.p. 107° C. at 3 mm Hg, 92% yield).

後処理

  1. customInto a round bottom flask was placed
  2. temperatureThe mixture then was refluxed under nitrogen for 8 hr
  3. customThe cooled reaction mixture
  4. extractionthe solution extracted with chloroform (5×25 mL)
  5. dry with materialThe combined organic liquors were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. distillationand the resulting oil distilled under reduced pressure

出典と根拠

ORDレコード
ord-acfd98fbecaf4acda872324b5f557a19
出典データセット
uspto-grants-1998_03
特許番号
US05726316

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