Tetrahydrofuran → [2-(Methylamino)pyridin-3-yl]methanol

HRID 2194511Notes

Reaction equation

HRID 2194511 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][NH:13][C:14]1[N:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].[OH-].[Na+]>C(OCC)(=O)C>[CH3:12][NH:13][C:14]1[C:15]([CH2:16][OH:17])=[CH:19][CH:20]=[CH:21][N:22]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 47385172-(methylamino)pyridine-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 4738518[2-(Methylamino)pyridin-3-yl]methanolYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen gas stream, 14.4 g (0.38 mol) of lithium aluminum hydride was added to tetrahydrofuran (300 mL) under ice cooling, and a tetrahydrofuran (100 mL) solution of crude 2-(methylamino)nicotinic acid was added dropwise to the above mixture. The resulting mixture was stirred overnight at room temperature. Ethyl acetate was added to the reaction mixture, and 152 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 was purified by column chromatography (ethyl acetate:n-hexane=1:1 to 4:1). Thus, 9.10 g (yield: 35%) of the title compound was obtained as a pale yellow viscous product.

Workup

  1. additionwas further added
  2. filtrationInsoluble materials were filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography (ethyl acetate:n-hexane=1:1 to 4:1)

Sources & evidence

ORD record
ord-1e39341b55094968ae7a0c5111c4e652
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

Loading…