Diphenyl Ether → 6-(Thiazol-2-yl)nicotinic acid

HRID 1200025Notes

Reaction equation

HRID 1200025 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][CH2:12][CH2:13][N:14]=2)=[N:8][CH:9]=1)([OH:3])=[O:2].C1(OC2C=CC=CC=2)C=CC=CC=1>CO.[Pd]>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][CH:9]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 7583Diphenyl EtherHCID 198645865-Carboxy-2-(4,5-dihydro-2-thiazolyl)-pyridine

Product 1

HCID 198645836-(Thiazol-2-yl)nicotinic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 500 mg (2.4 mmol) of 5-carboxy-2-(4,5-dihydro-2-thiazolyl)-pyridine, 50 mg of 10% Pd on C and 5 g of diphenylether is refluxed for 4 h. The mixture is then diluted with methanol and the catalyst filtered off. The methanol is evaporated and some hexane added to the residue. The diphenylether dissolves and a solid is left, which is filtered off and washed with hexane. This residue is dissolved again in methanol and treated with charcoal. After evaporation of the methanol the title compound, m.p. >300°, is obtained.

Workup

  1. temperatureis refluxed for 4 h
  2. filtrationthe catalyst filtered off
  3. customThe methanol is evaporated
  4. additionsome hexane added to the residue
  5. dissolutionThe diphenylether dissolves
  6. waita solid is left
  7. filtrationwhich is filtered off
  8. washwashed with hexane
  9. dissolutionThis residue is dissolved again in methanol
  10. additiontreated with charcoal
  11. customAfter evaporation of the methanol the title compound, m.p. >300°
  12. customis obtained

Sources & evidence

ORD record
ord-747d791c1d104d878db7f36bb341dfa9
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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