Pyridinium chloride → HCID 13985632, compound

HRID 485882Notes

Reaction equation

HRID 485882 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18]C.Cl.N1C=CC=CC=1>O>[Cl:1][C:2]1[C:7]2[S:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:18]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290185HCID 13290185, compound

Product 1

HCID 13985632HCID 13985632, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 9.5 g of 7-chloro-3-(2-fluorophenyl)-6-methoxybenzo[b]thiophene and 80 g of pyridine hydrochloride is heated at 190° C. for 7 hours, with stirring. Water (500 ml) is added to the cooled reaction mixture and the resulting suspension is extracted with ether (3 times). The combined etheral extracts are cooled with dilute hydrochloric acid, dried over anhydrous magnesium sulfate and evaporated to afford 8.9 g of 7-chloro-6-hydroxy-3-(2-fluorophenyl)benzo[b]thiophene.

Workup

  1. extractionthe resulting suspension is extracted with ether (3 times)
  2. temperatureThe combined etheral extracts are cooled with dilute hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-7cf1e45d6551467880d21c49828c569e
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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