Lithium aluminum hydride → 6-[(3-Chloro-pyridin-4-ylmethyl)-amino]pyridin-3-yl-methanol

HRID 1024259Notes

Reaction equation

HRID 1024259 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[Cl:18])=[N:6][CH:5]=1.[AlH4-].[Li+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:18][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:12]=1[CH2:11][NH:10][C:7]1[N:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 28112Lithium aluminum hydrideHCID 62649Sodium sulfate decahydrateHCID 576192956-[(3-Chloro-pyridin-4-ylmethyl)-amino]-nicotinic acid methyl ester

Product 1

HCID 576192366-[(3-Chloro-pyridin-4-ylmethyl)-amino]pyridin-3-yl-methanolYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-[(3-chloro-pyridin-4-ylmethyl)-amino]-nicotinic acid methyl ester (555, 1.00 g, 3.60 mmol) in tetrahydrofuran (120 mL) was added a solution of lithium tetrahydroaluminate (1.00M in tetrahydrofuran, 5.00 mL) under an atmosphere of nitrogen at room temperature. The reaction was stirred at room temperature overnight, followed with addition of sodium sulfate decahydrate. After 1 hour, the reaction mixture was filtered, concentrated, and purified with silica gel column chromatography eluting with 2% to 20% methanol in dichloromethane to give the desired compound as a white solid (556, 0.5 g, 56%). MS (ESI) [M+H+]+=250.1.

Workup

  1. waitAfter 1 hour
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified with silica gel column chromatography
  5. washeluting with 2% to 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-7a72b6f7747e4d859a29f132045db877
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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