Pyridine → 2,5-Dihydroxybenzonitrile

HRID 1733806Notes

Reaction equation

HRID 1733806 reaction equation
FC(F)(F)C(O[C:6](=[O:11])[C:7](F)(F)F)=O.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Cl)Cl.C1C[O:26]CC1>>[C:15]([C:16]1[CH:7]=[C:6]([OH:11])[CH:19]=[CH:18][C:17]=1[OH:26])#[N:14]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 9845Trifluoroacetic anhydride

Product 1

HCID 783742,5-DihydroxybenzonitrileYield 68%

Procedure

Trifluoroacetic anhydride (3.06 mL, 22 mmoles) was added dropwise to a stirred, ice-cooled solution of 34 (770 mg, 5.0 mmoles) in 10 mL of dry THF and anhydrous pyridine (3.23 mL, 40 mmoles) at such a rate that the temperature was kept below 5° C. The addition was over in 30 minutes. The reaction mixture was then allowed to warm to room temperature and stirred for another 16 hr. 650 mL of CH2Cl2 was added and the organic solution was washed with water (3×10 mL) and saturated brine (3×15 mL), dried on Na2SO4 and evaporated under reduced pressure. The crude product was applied to silica gel (230-400 mesh, ethyl acetate) to yield 462 milligrams (68%) of 20.

Workup

  1. customwas kept below 5° C
  2. additionThe addition
  3. customwas over in 30 minutes
  4. washthe organic solution was washed with water (3×10 mL) and saturated brine (3×15 mL)
  5. customdried on Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-05690bb2e0b9460fa73c8456d65c5cc5
Source dataset
uspto-grants-1996_07
Patent number
US05532138

Reaction notes

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