Sodium Hydroxide → 5-(2-Hydroxypropan-2-yl)nicotinic acid

HRID 1048954Notes

Reaction equation

HRID 1048954 reaction equation
[OH:1][C:2]([C:5]1[CH:6]=[C:7]([C:11]([O:13]C)=[O:12])[CH:8]=[N:9][CH:10]=1)([CH3:4])[CH3:3].[OH-].[Na+]>CO>[OH:1][C:2]([C:5]1[CH:6]=[C:7]([C:11]([OH:13])=[O:12])[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66684512Methyl 5-(2-hydroxypropan-2-yl)pyridine-3-carboxylate

Product 1

HCID 680538445-(2-Hydroxypropan-2-yl)nicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-(2-hydroxypropan-2-yl)pyridine-3-carboxylate (0.179 g, 0.915 mmol) in methanol (4.57 mL) was added 1 N aqueous sodium hydroxide solution (2.74 mL, 2.74 mmol). The reaction was stirred at room temperature for 30 min and then concentrated under reduced pressure. The resulting residue was acidified via the addition of 1 N aqueous hydrogen chloride solution until the pH was 2. Ethyl acetate was then added, and the extracted organics were dried over magnesium sulfate, filtered and concentrated to provide the title compound: LCMS m/z 182.01 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.91 (s, 1 H), 8.79 (d, J=1.8 Hz, 1 H), 8.43 (d, J=1.9 Hz, 1 H), 1.51 (s, 6 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was acidified via the addition of 1 N aqueous hydrogen chloride solution until the pH was 2
  3. additionEthyl acetate was then added
  4. dry with materialthe extracted organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-78ab0b566fc74db8b9bf404a608b787c
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

Loading…