Ethanol → 3-Chloro-5-(hydroxymethyl)benzamide

HRID 1260866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260866
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[C:7](OC)=[O:8])=[O:3].C(O)C.[BH4-].[Li+]>O1CCCC1>[Cl:14][C:12]1[CH:13]=[C:4]([CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=1)[C:2]([NH2:1])=[O:3]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 58963003Methyl 3-carbamoyl-5-chlorobenzoate

Produkt 1

HCID 589629763-Chloro-5-(hydroxymethyl)benzamideAusbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(Step 1) To a mixed solution of methyl 3-(aminocarbonyl)-5-chlorobenzoate (2.2 g) in tetrahydrofuran:ethanol=10:1 (33 ml) was added lithium tetrahydroborate (0.34 g) at room temperature. After stirring at 60° C. for 2 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=5:1) to give 3-chloro-5-(hydroxymethyl)benzamide (0.95 g).

Aufarbeitung

  1. customthe reaction solution was quenched with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionthe obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-15baf875d4e64000b1190902858adec3
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470859B2

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