Chlorosuccinimide → 2-[(3-Chloro-2-hydroxymethyl-pyridin-4-yl)-methylamino]-ethanol

HRID 1637627ノート

反応式

HRID 1637627 の反応式
[Cl:1]N1C(=O)CCC1=O.[OH:9][CH2:10][C:11]1[CH:16]=[C:15]([N:17]([CH3:21])[CH2:18][CH2:19][OH:20])[CH:14]=[CH:13][N:12]=1>C(O)(=O)C>[Cl:1][C:16]1[C:11]([CH2:10][OH:9])=[N:12][CH:13]=[CH:14][C:15]=1[N:17]([CH3:21])[CH2:18][CH2:19][OH:20]

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 187993842-[(2-Hydroxymethyl-pyridin-4-yl)-methyl-amino]-ethanol

生成物 1

HCID 537528042-[(3-Chloro-2-hydroxymethyl-pyridin-4-yl)-methylamino]-ethanol

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

N-Chlorosuccinimide (25 g, 187 mmol) is added in 5 portions to a solution of 2-[(2-hydroxymethyl-pyridin-4-yl)-methyl-amino]-ethanol (30 g of the crude product isolated in step a), 140 mmol) in acetic acid (170 ml) over a period of 3 h. Stirring is continued for I h and the solvent is evaporated in vacuo. The residue is treated with 6N sodium hydroxide solution and extracted with ethyl acetate. The combined organic extracts are washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue is chromatographed (silica, toluene/dioxane 2:1) to give the title compound as a brown solid. M.p. 49-53° C.

後処理

  1. customthe solvent is evaporated in vacuo
  2. additionThe residue is treated with 6N sodium hydroxide solution
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue is chromatographed (silica, toluene/dioxane 2:1)

出典と根拠

ORDレコード
ord-0f5d6ba912894d34b2a78b56778cc574
出典データセット
uspto-grants-2000_03
特許番号
US06043242

反応ノート

読み込み中…