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

HRID 1927252Notes

Reaction equation

HRID 1927252 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].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>C1COCC1>[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 hydride2×HCID 592553992-Amino-6-methoxymethyl-nicotinic acid methyl ester

Product 1

HCID 59255403(2-Amino-6-methoxymethyl-pyridin-3-yl)methanolYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of LAH (80%, 220 mg) and THF (5 mL) was added 2-amino-6-methoxymethyl-nicotinic acid methyl ester (300 mg) described in Manufacturing Example 11-3 at 0° C., which was stirred for 20 minutes at the same temperature. A 28% aqueous ammonia solution was added dropwise to the reaction mixture at the same temperature until the LAH was inactivated. The reaction mixture was warmed to room temperature and filtered. The filtrate was evaporated under a reduced pressure to obtain the titled compound (260 mg).

Workup

  1. customdescribed in Manufacturing Example 11-3 at 0° C.
  2. filtrationfiltered
  3. customThe filtrate was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-cbfad7b6d0ed425ea2e10deed9424876
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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