4-Toluenesulfonyl chloride → HCID 68139828, compound

HRID 267986Notes

Reaction equation

HRID 267986 reaction equation
[N:1]1([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:15]=2[CH:14]=[N:13][CH:12]=[CH:11]3)[CH:5]=[CH:4][CH:3]=[CH:2]1.[C-:16]#[N:17].[K+].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl.O>[C:16]([CH:14]1[C:15]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)[CH:11]=[CH:12][N:13]1[S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)(=[O:27])=[O:26])#[N:17]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 9032Potassium CyanideHCID 21552906HCID 21552906, compound

Product 1

HCID 68139828HCID 68139828, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

8-(Pyrrol-1-yl)isoquinoline (293 g.) and potassium cyanide (295 g.) are dissolved in a mixture of methylene chloride (880 cc.) and water (880 cc.) and the solution stirred at a temperature of between 0° and 5° C. After adding a solution of toluene-p-sulphonyl chloride (575 g.) in methylene chloride (880 cc.) over the course of 45 hours, decanting and then washing the organic solution with water, a solid brown residue is obtained. After recrystallisation from acetonitrile (750 cc.), this crude product yields 1-cyano-8-(pyrrol-1-yl)-2-toluene-p-sulphonyl-1,2-dihydroisoquinoline (407 g.) melting at 160° C.

Workup

  1. customdecanting
  2. washwashing the organic solution with water
  3. customa solid brown residue is obtained
  4. customAfter recrystallisation from acetonitrile (750 cc.)

Sources & evidence

ORD record
ord-9e44e430b16f405abf3ff467d4646693
Source dataset
uspto-grants-1976_03
Patent number
US03946019

Reaction notes

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