Pyridinium chloride → HCID 10420259, compound

HRID 1275529Notes

Reaction equation

HRID 1275529 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C:8]3[C:13]([O:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.Cl.N1C=CC=CC=1>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C:8]3[C:13]([O:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 14966062HCID 14966062, compound

Product 1

HCID 10420259HCID 10420259, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solid mixture of 3-methoxy-9H-xanthene 9 (5.84 g, 27.5 mmole) and pyridine hydrochloride (42 g, 363 mmole) was heated at 200-210° for 2 hrs. The resulting reaction mixture was cooled to about 70° and treated with water, while a precipitate formed. The orange colored solid was filtered on a Buchner funnel, washed with water, and dried in vacuo, yielding the crude 3-hydroxy-9H-xanthene 10 (5.25 g, 96%). No major oxidation took place when crude 10 was stored in a desiccator under argon in the dark. Thus, the crude xanthene 10 was used for silylation without further purification. No 1H NMR or 1R were taken.

Workup

  1. temperaturewas heated at 200-210° for 2 hrs
  2. customThe resulting reaction mixture
  3. temperaturewas cooled to about 70°
  4. customformed
  5. filtrationThe orange colored solid was filtered on a Buchner funnel
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ba24539db29542969215eecc50b16455
Source dataset
uspto-grants-2000_12
Patent number
US06162610

Reaction notes

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