1-Propanol, 2-methyl-, sodium salt (1:1) → HCID 67486093, compound

HRID 1431000Notes

Reaction equation

HRID 1431000 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:15][CH:16]([CH2:18][O-:19])[CH3:17].[Na+]>>[CH2:18]([O:19][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[N:10]=1)[C:5]([OH:7])=[O:6])[CH:16]([CH3:17])[CH3:15]

Participants

3

Reactant 2

HCID 236737041-Propanol, 2-methyl-, sodium salt (1:1)HCID 431665512-Chloro-6-[(propan-2-yl)oxy]pyridine-4-carboxylic acid

Product 1

HCID 67486093HCID 67486093, compoundYield 25%

Conditions

Temperature
210 °C

Procedure

To a flask containing 2-chloro-6-isopropoxyisonicotinic acid (1.05 g, 4.83 mmol) was added 28 mL (9.66 mmol) of freshly prepared sodium isobutoxide (0.35 M in isobutanol). This mixture was split evenly into two 20 mL microwave vials and each vial was heated under microwave irradiation at 210° C. for 20 min. The reaction mixture was purified by C18 medium pressure chromatography using a gradient of acetonitrile in water to afford 310 mg (25%) of 2-isobutoxy-6-isopropoxyisonicotinic acid. 1H NMR (300 MHz, DMSO-d6) δ 0.95 (d, 6H, J=7 Hz), 1.27 (d, 61-1, J=6 Hz), 1.96-2.05 (m, 1H), 3.96 (d, 2H, J=7 Hz), 5.05-5.13 (m, 1H), 6.59 (s, 1H), 6.63 (s, 1H).

Workup

  1. customThis mixture was split evenly into two 20 mL microwave vials
  2. customThe reaction mixture was purified by C18 medium pressure chromatography

Sources & evidence

ORD record
ord-481e3d10e4ef44e9bb38a4652e6c5967
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

Loading…