Tetrahydrofuran → (2-Anilinopyridin-3-yl)methanol

HRID 2194525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194525
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]1([NH:18][C:19]2[N:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21](O)=[O:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>C(OCC)(=O)C>[C:12]1([NH:18][C:19]2[C:20]([CH2:21][OH:22])=[CH:24][CH:25]=[CH:26][N:27]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 14817992-Anilinonicotinic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 13986159(2-Anilinopyridin-3-yl)methanolAusbeute 108,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Under a nitrogen gas stream, 2.41 g (63.4 mmol) of lithium aluminum hydride was added to tetrahydrofuran (80 mL) under ice cooling, and a tetrahydrofuran (30 mL) solution of 6.79 g (31.7 mmol) of 2-(phenylamino)nicotinic acid was added dropwise to the above solution. The resulting mixture was stirred for 2 hours at room temperature. Ethyl acetate was added to the reaction mixture, and 25 mL of a 10% aqueous solution of sodium hydroxide was further added thereto. Insoluble materials were filtered off. The filtrate was concentrated, and the residue thus obtained was dissolved in ethyl acetate, dried, filtered, and concentrated. Thus, 6.9 g of the title compound was obtained as a yellow viscous product (yield: quantitative).

Aufarbeitung

  1. additionwas further added
  2. filtrationInsoluble materials were filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue thus obtained
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-05ffb3b666654e4e944b06fc396c8e6c
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334236B2

Notizen zur Reaktion

Wird geladen…