Pyridine → HCID 18691296, compound

HRID 376315Notes

Reaction equation

HRID 376315 reaction equation
[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N+:9]([O-])[CH:8]=[CH:7]2.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N:26]1C=CC=CC=1>>[NH2:26][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:13][CH3:14])[C:2]=2[Cl:1])[CH:7]=[CH:8][N:9]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 18691278HCID 18691278, compound

Product 1

HCID 18691296HCID 18691296, compound

Procedure

To a solution of 1.3 g of 8-chloro-7-methoxyisoquinoline-N-oxide in 40 ml of pyridine was added 1.4 g of p-toluenesulfonyl chloride, and the mixture was stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure, 20 ml of ethanolamine was added to the resultant residue, and then the mixture was stirred for further 3 hours. The reaction mixture was poured into water, and the crystalline precipitate was collected by filtration, washed with water, and dried under reduced pressure to give 0.8 g of the title compound as a yellow powder.

Workup

  1. customThe solvent was removed under reduced pressure, 20 ml of ethanolamine
  2. additionwas added to the resultant residue
  3. stirringthe mixture was stirred for further 3 hours
  4. additionThe reaction mixture was poured into water
  5. filtrationthe crystalline precipitate was collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-ff4d6d8df80347588328d4f58012d343
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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