Ammonia → (2-Amino-6-methoxymethyl-pyridin-3-yl)methanol

HRID 1693803Notes

Reaction equation

HRID 1693803 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][CH3:18])=[N:12][C:11]=1[NH2:19].N>O1CCCC1>[NH2:19][C:11]1[C:10]([CH2:9][OH:8])=[CH:15][CH:14]=[C:13]([CH2:16][O:17][CH3:18])[N:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 21226445Aluminium lithium hydrideHCID 592553992-Amino-6-methoxymethyl-nicotinic acid methyl ester

Product 1

HCID 59255403(2-Amino-6-methoxymethyl-pyridin-3-yl)methanolYield 103.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of lithium aluminum hydride (80%, 220 mg, 4.6 mmol) and tetrahydrofuran (5 mL) was added 2-amino-6-methoxymethyl-nicotinic acid methyl ester (300 mg, 1.5 mmol) described in Manufacturing Example 26-1-4 at 0° C., which was stirred for 20 minutes at the same temperature. An aqueous 28% ammonia solution was added dropwise to the reaction mixture at 0° C. The mixture was warmed to room temperature and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (260 mg, 100%).

Workup

  1. customdescribed in Manufacturing Example 26-1-4 at 0° C.
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-65c64a17ea224b269d69ee3d4561c179
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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