m-Chloroperbenzoic acid → 4-Chloro-5,6-dihydroquinoline

HRID 1613591Notes

Reaction equation

HRID 1613591 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([Se]C3C=CC=CC=3)[C:6]=2[N:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]=[CH:7][C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 148359614-Chloro-5,6,7,8-tetrahydro-8-(phenylseleno)quinoline

Product 1

HCID 148359624-Chloro-5,6-dihydroquinolineYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from the product of Step 3 (9 g, 28 mmol), 86% 3-chloroperoxybenzoic acid (5.8 g, 29 mmol), and dichloromethane (150 ml) using the procedure outlined in Example 25. Step 2. Distillation gave the product (4.35 g) as an oil.

Workup

  1. distillationDistillation

Sources & evidence

ORD record
ord-d9a66b36368f49dea5235a76e3858063
Source dataset
uspto-grants-1993_03
Patent number
US05194439

Reaction notes

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