Toluene → 2-Amino-6-(2-cyanoethyl)-nicotinic acid methyl ester

HRID 2079950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079950
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[N:6][C:5]=1[NH2:12].[C-:14]#[N:15].C([Al+]CC)C.C1(C)C=CC=CC=1.[Cl-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:14]#[N:15])=[N:6][C:5]=1[NH2:12]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 5234Sodium ChlorideHCID 16686413Diethyl aluminum cyanideHCID 583190542-Amino-6-vinyl-nicotinic acid methyl ester

Produkt 1

HCID 583879902-Amino-6-(2-cyanoethyl)-nicotinic acid methyl esterAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-6-vinyl-nicotinic acid methyl ester (760 mg, 4.26 mmol) in tetrahydrofuran (76 mL) was added a solution of diethyl aluminum cyanide in toluene (12.8 mL, 12.8 mmol) dropwise under sodium chloride—an ice bath cooling, at an internal temperature of −5° C. or below, then, the solution was gradually allowed to room temperature and stirred overnight. The reaction solution was partitioned into an aqueous solution of saturated ammonium chloride and ethyl acetate. This organic layer was separated, washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography, and the title compound (180 mg, 0.878 mmol, 21%) was obtained as a yellow oil.

Aufarbeitung

  1. temperaturecooling, at an internal temperature of −5° C. or below
  2. customwas gradually allowed to room temperature
  3. customThe reaction solution was partitioned into an aqueous solution of saturated ammonium chloride and ethyl acetate
  4. customThis organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1fad45fe537746ec9e4f9f66498ed0a5
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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