Aluminium lithium hydride → N-Methyl-N-[(1-methyl-1H-indazol-3-yl)methyl]amine

HRID 1710487

Reaktionsgleichung

Reaktionsgleichung von HRID 1710487
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[N:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:14][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH2:3][NH:2][CH3:1])=[N:6]1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 22593809N,1-dimethyl-1H-indazole-3-carboxamide

Produkt 1

HCID 7537473N-Methyl-N-[(1-methyl-1H-indazol-3-yl)methyl]amineAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of N,1-dimethyl-1H-indazole-3-carboxamide (3.42 g, 18 mmole) in dry THF (90 mL) was added a solution of LiAlH4 in THF (1.0 M, 36 mL, 36 mmole) slowly at RT. After 2 hr the mixture was heated to a gentle reflux. After 4 hr the mixture was cooled to RT and quenched by dropwise addition of 2.0 M NaOH until a white solid had formed. The mixture was dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (3.28 g, 100%) as an oil which was sufficiently pure for use in the next step: MS (ES) m/e 176 (M+H)+.

Aufarbeitung

  1. temperatureAfter 2 hr the mixture was heated to a gentle reflux
  2. customquenched by dropwise addition of 2.0 M NaOH until a white solid
  3. customhad formed
  4. dry with materialThe mixture was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c101ae9b67364dc3a978e0c2625cde97
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790716B2

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