Methanol → 5-Chloro-6-methoxypyridine-3-carboxylic acid

HRID 1908781Notes

Reaction equation

HRID 1908781 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][OH:13]>O>[Cl:1][C:2]1[C:3]([O:13][CH3:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 167853775-Chloro-6-methoxypyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5,6-Dichloro-nicotinic acid (1.00 g, 5.21 mmol) is added to a solution of Na (252 mg, 10.9 mmol) in methanol (50 mL). The mixture is refluxed overnight before another portion of Na (252 mg, 10.9 mmol) is added. Refluxing is continued for 2 h. The mixture is cooled to rt, diluted with water and concentrated. The remaining solid is dissolved in water and the solution is neutralised by adding 2 N aq. HCl. The resulting suspension is extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give 5-chloro-6-methoxy-nicotinic acid (976 mg) as a white solid; LC-MS: tR=0.77 min; [M+1]+=189.90; 1H NMR (D6-DMSO): δ 4.03 (s, 3H), 8.22 (d, J=1.8 Hz, 1H), 8.67 (d, J=2.0 Hz, 1H).

Workup

  1. additionis added
  2. temperatureRefluxing
  3. concentrationconcentrated
  4. dissolutionThe remaining solid is dissolved in water
  5. additionby adding 2 N aq. HCl
  6. extractionThe resulting suspension is extracted twice with EA
  7. dry with materialextracts are dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried

Sources & evidence

ORD record
ord-afac8c37ed5d403fb1ea16a1852a3bb4
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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