Acetic Acid → 2-Amino-6-methoxymethylnicotinic acid

HRID 2079944Notes

Reaction equation

HRID 2079944 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][CH3:15])=[N:9][C:8]=1[NH2:16].O1CCCC1.C(O)(=O)C>O.CO>[NH2:16][C:8]1[N:9]=[C:10]([CH2:13][O:14][CH3:15])[CH:11]=[CH:12][C:7]=1[C:6]([OH:17])=[O:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 592553992-Amino-6-methoxymethyl-nicotinic acid methyl ester

Product 1

HCID 231304372-Amino-6-methoxymethylnicotinic acidYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide monohydrate (1.2 g, 29 mmol) was added to a mixture of 2-amino-6-methoxymethyl-nicotinic acid methyl ester described in Preparation Example A-10 (2.9 g, 15 mmol), tetrahydrofuran (30 mL), methanol (7.5 mL), and water (7.5 mL), which was then stirred overnight at room temperature. Acetic acid (1.7 mL, 29 mmol) was added to the reaction solution and the solvent was evaporated in vacuo. After filtration using silica gel (methanol/ethyl acetate=1/3) and the solvent was evaporated in vacuo, the residue was washed with water, and the title compound (2.1 g, 12 mmol, 80%) was obtained as a pale yellow solid.

Workup

  1. customthe solvent was evaporated in vacuo
  2. filtrationAfter filtration
  3. customthe solvent was evaporated in vacuo
  4. washthe residue was washed with water

Sources & evidence

ORD record
ord-7cf66f8d53cb4c94bf6a0075855c7a3f
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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