Tetrahydrofuran → HCID 67009976, compound

HRID 2194520Notes

Reaction equation

HRID 2194520 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][O:13][C:14]1[CH:30]=[CH:29][CH:28]=[CH:27][C:15]=1[CH2:16][NH:17][C:18]1[N:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=[O:21].[OH-].[Na+]>C(OCC)(=O)C>[CH3:12][O:13][C:14]1[CH:30]=[CH:29][CH:28]=[CH:27][C:15]=1[CH2:16][NH:17][C:18]1[C:19]([CH2:20][OH:21])=[CH:23][CH:24]=[CH:25][N:26]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 257062592-{[(2-Methoxyphenyl)methyl]amino}pyridine-3-carboxylic acid

Product 1

HCID 67009976HCID 67009976, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Under a nitrogen gas stream, 2.50 g (65.8 mmol) of lithium aluminum hydride was added to tetrahydrofuran (100 mL) under ice cooling, and a tetrahydrofuran (70 mL) solution of 8.50 g (32.9 mmol) of 2-(2-methoxybenzylamino)nicotinic acid was added dropwise to the above solution. The resulting mixture was stirred for one hour at room temperature. Ethyl acetate was added to the reaction mixture, and then 26.4 mL of a 10% aqueous solution of sodium hydroxide was 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, 8.18 g (yield: quantitative) of the title compound was obtained as a pale yellow viscous product.

Workup

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

Sources & evidence

ORD record
ord-694e6d8ac8224f14aca62f9d4401fb37
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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