Pyridinium chloride → HCID 13290005, compound

HRID 370948Notes

Reaction equation

HRID 370948 reaction equation
[Cl:1][C:2]1[C:3]([O:13]C)=[CH:4][C:5]2[C:9]([CH3:10])=[CH:8][S:7][C:6]=2[C:11]=1[Cl:12].Cl.N1C=CC=CC=1>O>[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][C:5]2[C:9]([CH3:10])=[CH:8][S:7][C:6]=2[C:11]=1[Cl:12]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290004HCID 13290004, compound

Product 1

HCID 13290005HCID 13290005, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.6 g of 6,7-dichloro-5-methoxy-3-methylbenzo[b]thiophene and 50 g of pyridine hydrochloride is stirred at 190°-195° for 2 hours. The cooled reaction mixture is diluted with water and extracted with three 300 ml-portions of ether. The combined ether extracts are washed, dried and concentrated to give a tan-colored solid, mp 137°-139°. Recrystallization from hexane gives 3.8 g of 6,7-dichloro-5-hydroxy-3-methylbenzo[b]thiophene as silky needles.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with three 300 ml-portions of ether
  3. washThe combined ether extracts are washed
  4. customdried
  5. concentrationconcentrated
  6. customto give a tan-colored solid, mp 137°-139°
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-39705d86d0ba40a1ab82d6541661dfe5
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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