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

HRID 1637627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637627
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0f5d6ba912894d34b2a78b56778cc574
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043242

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