4-Chlorophenol → 6-Chloro-9-(4-chlorophenoxy)-2-methoxyacridine

HRID 440614Notes

Reaction equation

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

Participants

Reactant 3

HCID 46844-Chlorophenol

HCID 14798Sodium Hydroxide

HCID 665773,9-Dichloro-7-methoxyacridine

Product 1

HCID 224072856-Chloro-9-(4-chlorophenoxy)-2-methoxyacridine

Conditions

Temperature: 80 °C

Procedure

A reaction mixture consisting of 1.39 g (5.0 mmol) of 6,9-dichloro-2-methoxyacridine and 3.0 g (23 mmol) of p-chlorophenol was heated at 80° C. for 4 h. The hot reaction mixture was poured into hot 5% aqueous NaOH. The combined solution was stirred until a fine yellow crystalline precipitate appeared. The crystals were filtered, washed to neutrality with water and dried at 70° C. in vacuo. Recrystallization from pyridine afforded 6-chloro-9-(p-chlorophenoxy)-2-methoxyacridine as yellow microcrystals, yield 1.06 g (57%), mp 151.5°-153° C.; λ max (CH3OH) 400, 381, 351, 333, 318 (sh) and 262 nm; 1H-NMR (CDCl3, (CH3)4Si) δ 3.76 (s, 3) 6.7-6.9 (m, 2) 7.1-7.6 (m, 5) and 7.8-8.2 (m, 3).

Workup

filtrationThe crystals were filtered
washwashed
customdried at 70° C. in vacuo
customRecrystallization from pyridine

Sources & evidence

ORD record: ord-07f2f0c1a7b14fd3872fbdfd3a1cac9b
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05519126

Reaction notes

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