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

HRID 1367373Notes

Reaction equation

HRID 1367373 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 (1.00 M 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-b61ec96570af45a09a27fec9ad1d1262
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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