Methanol → 2-Amino-6-methoxymethylnicotinic acid

HRID 1927240Notes

Reaction equation

HRID 1927240 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH3:12])=[N:6][C:5]=1[NH2:13].C1COCC1.CO.O.[OH-].[Li+]>C(O)(=O)C.O>[NH2:13][C:5]1[N:6]=[C:7]([CH2:10][O:11][CH3:12])[CH:8]=[CH:9][C:4]=1[C:3]([OH:14])=[O:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 592553992-Amino-6-methoxymethyl-nicotinic acid methyl ester

Product 1

HCID 231304372-Amino-6-methoxymethylnicotinic acidYield 78%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of 2-amino-6-methoxymethyl-nicotinic acid methyl ester (2.9 g) described in Manufacturing Example 11-3, THF (30 mL), methanol (7.5 mL), and water (7.5 mL) was added lithium hydroxide monohydrate (1.2 g), which was stirred overnight at room temperature. Acetic acid (1.7 mL of) was added to the reaction mixture at the same temperature, and the solvent was evaporated under a reduced pressure. The residue was filtered through silica gel (methanol:ethyl acetate=1:3) and the solvent was evaporated under a reduced pressure, after which the residue was washed with water to obtain the titled compound (2.1 g).

Workup

  1. customthe solvent was evaporated under a reduced pressure
  2. filtrationThe residue was filtered through silica gel (methanol:ethyl acetate=1:3)
  3. customthe solvent was evaporated under a reduced pressure
  4. washafter which the residue was washed with water

Sources & evidence

ORD record
ord-840af2f3ead24fce817e55416fbd8538
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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