2,6-Dichloroisonicotinic acid → 2-Chloro-6-[(propan-2-yl)oxy]pyridine-4-carboxylic acid

HRID 1430999Notes

Reaction equation

HRID 1430999 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:12][CH:13]([CH3:15])[O-:14].[Na+]>C(O)(C)C>[Cl:11][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([O:14][CH:13]([CH3:15])[CH3:12])[N:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 948302,6-Dichloroisonicotinic acidHCID 109204432-Propanol, sodium salt (1:1)

Product 1

HCID 431665512-Chloro-6-[(propan-2-yl)oxy]pyridine-4-carboxylic acidYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2,6-dichloroisonicotinic acid (1.26 g, 6.56 mmol) in isopropanol (20 mL) was added 27 mL (16.40 mmol) of freshly made sodium isopropoxide (0.61 M in isopropanol). This mixture was split evenly into four 20 mL microwave vials and each vial was heated under microwave irradiation at 150° C. for 10 min. The combined reaction solutions were eluted through a column of Dianion HP-20 PS resin eluting first with water followed by 100% acetonitrile to provide 770 mg (54%) of 2-chloro-6-isopropoxyisonicotinic acid. 1H NMR (300 MHz, DMSO-d6) δ 1.27 (d, 6H, J=6 Hz), 5.08-5.14 (m, 1H), 6.95 (s, 1H), 7.23 (s, 1H)

Workup

  1. customThis mixture was split evenly into four 20 mL microwave vials
  2. customThe combined reaction solutions
  3. washwere eluted through a column of Dianion HP-20 PS resin
  4. washeluting first with water

Sources & evidence

ORD record
ord-76e57978092e431ea24e38a804945d1e
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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