2,4-Dichlorophenol → 5-(2,4-Dichlorophenoxy)-6-methoxy-4-methyl-8-nitroquinoline

HRID 1388573Notes

Reaction equation

HRID 1388573 reaction equation
Cl[C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[C:4]([CH3:17])=[CH:5][CH:6]=[N:7]2.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[OH:26].[OH-].[K+]>C(OCCO)C>[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[C:4]([CH3:17])=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 14797Potassium HydroxideHCID 120499275-Chloro-6-methoxy-4-methyl-8-nitroquinoline

Product 1

HCID 130042025-(2,4-Dichlorophenoxy)-6-methoxy-4-methyl-8-nitroquinoline

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

The title compound was prepared from 5-chloro-6-methoxy-4-methyl-8-nitroquinoline from Example 1 (15 g, 0.06 mol), 2,4-dichlorophenol (38 g, 0.23 mol), potassium hydroxide (13.2 g, 0.24 mol) and 2-ethoxyethanol (150 mL) as described in Example 1. The yield was 14.5 g (64%), mp 165.5°-168°.

Sources & evidence

ORD record
ord-202121100b9f46e8903a24807ea3596b
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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