Hydrochloric Acid → (3-Amino-6-chloropyridin-2-yl)methanol

HRID 475327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475327
[NH2:1][C:2]1[C:3]([C:9](O)=[O:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.B.C1COCC1.Cl.C([O-])(O)=O.[Na+]>C1COCC1.O>[NH2:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 533934343-Amino-6-chloropyridine-2-carboxylic acid

Produkt 1

HCID 19353056(3-Amino-6-chloropyridin-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3-amino-6-chloro-pyridine-2-carboxylic acid (95 mg, 0.55 mmol) is taken up in THF (1 mL) and combined with BH3-THF complex (2.2 mL, 2.2 mmol, 1 M in THF). The reaction mixture is stirred for 2 d at 20° C. The reaction is ended with dilute HCl and H2O, then neutralised with NaHCO3, extracted with EtOAc, the organic phase is dried on MgSO4, the solvent is eliminated in vacuo and (3-amino-6-chloro-pyridin-2-yl)-methanol is obtained (HPLC-MS: tRet.=0.79 min, MS(M+H)+=159; method AFEC).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customthe organic phase is dried on MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-af812f5ad6794187ae9e247e4dfa5dae
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637549B2

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