Lithium Hydroxide → 2-Amino-4,6-diisopropoxy-nicotinic acid

HRID 591783Notes

Reaction equation

HRID 591783 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[C:9]([O:10][CH:11]([CH3:13])[CH3:12])=[CH:8][C:7]([O:14][CH:15]([CH3:17])[CH3:16])=[N:6][C:5]=1[NH2:18].[OH-].[Li+]>CO.O>[NH2:18][C:5]1[N:6]=[C:7]([O:14][CH:15]([CH3:16])[CH3:17])[CH:8]=[C:9]([O:10][CH:11]([CH3:13])[CH3:12])[C:4]=1[C:3]([OH:19])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 666709872-Amino-4,6-diisopropoxy-nicotinic acid methyl ester

Product 1

HCID 666710672-Amino-4,6-diisopropoxy-nicotinic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To the solution of 2-amino-4,6-diisopropoxy-nicotinic acid methyl ester (1.6 g, 5.97 mmol) in methanol (9.0 mL) and water (1.0 mL), was added lithium hydroxide (750 mg, 17.91 mmol). The reaction mixture was heated to 50° C. for 8 hours. The solvent was removed; the residue was diluted with water and neutralized with 2 N HCl. The product was extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with water, then brine, dried over Na2SO4, and evaporated, to give crude 2-amino-4,6-diisopropoxy-nicotinic acid as a light yellow solid. Yield: 1.48 g (98%, crude).

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with water and neutralized with 2 N HCl
  3. extractionThe product was extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic layer was washed with water
  5. dry with materialbrine, dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-ada7c9549a194c1ba89326a121c6f78b
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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