Methyl 5-aminopyridine-3-carboxylate → (5-Aminopyridin-3-yl)methanol

HRID 548235Notes

Reaction equation

HRID 548235 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[N:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:10][C:8]1[CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 1514432Methyl 5-aminopyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 29921874(5-Aminopyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-nicotinic acid methyl ester (5.7 g, 30.2 mmol) was dissolved in THF (150 ml) and LiAlH4 (1M in THF solution 133 ml, 133 mmol) added slowly at 0° C. The reaction mixture was stirred at room temperature for 21 h. The reaction mixture was quenched and acidified to pH 3 using dilute HCl, and basified (pH 8) using solid Na2CO3. Solvents were removed under reduced pressure. The residue was filtered through silica gel using 20% MeOH/DCM yielding the product 3.8 g, (100%) with LCMS purity 97%, m/z 125 [M++H]+, by ELS.

Workup

  1. customThe reaction mixture was quenched
  2. customSolvents were removed under reduced pressure
  3. filtrationThe residue was filtered through silica gel using 20% MeOH/DCM yielding the product 3.8 g, (100%) with LCMS purity 97%, m/z 125 [M++H]+

Sources & evidence

ORD record
ord-aba6cc03212c405e89b4b5713114bf63
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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