Pyridinium chloride → HCID 13985632, compound

HRID 370973Notes

Reaction equation

HRID 370973 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-3807e85cdf774f27a8319e46c6f281ad
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

Loading…