6-(3-Cyanopropyloxy)nicotinic acid, methyl ester → 6-(3-Cyanopropyloxy)nicotinic acid

HRID 1634102Notes

Reaction equation

HRID 1634102 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][N:8]=1)#[N:2]>CO.O>[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=1)#[N:2]

Participants

3

Reactant 1

HCID 235516706-(3-Cyanopropyloxy)nicotinic acid, methyl ester

Product 1

HCID 186771166-(3-Cyanopropyloxy)nicotinic acidYield 85%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

6-(3-cyanopropyloxy)nicotinic acid, methyl ester (1.8 mmol) was dissolved in methanol/water (16 mL:4 mL) and treated with LiOH monohydrate (2.7 mmol). After stirring overnight, volatiles were removed and reaction neutralized with 1N sulfuric acid. The solid product was collected by filtration, washed with water and dried to give 6-(3-cyanopropyloxy)nicotinic acid (315 mg, 85%).

Workup

  1. customvolatiles were removed
  2. customreaction neutralized with 1N sulfuric acid
  3. filtrationThe solid product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b2e80849fd214f5b823e02b009c219d4
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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