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

HRID 1461287Notes

Reaction equation

HRID 1461287 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-0cedc83c4c054b22a1e11b48bd2008e1
Source dataset
uspto-grants-1991_12
Patent number
US05075303

Reaction notes

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