2,4-Dichloroaniline → 2-[3-(2,4-Dichlorophenylamino)-4-nitrophenyl]-2-methyl-1,3-dioxolane

HRID 1087183Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:11]2([CH3:16])[O:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Cl:17][C:18]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:19]=1[NH2:20].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Cl:17][C:18]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:19]=1[NH:20][C:2]1[CH:3]=[C:4]([C:11]2([CH3:16])[O:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2-(3-chloro-4-nitrophenyl)-2-methyl-1,3-dioxolane (8 g), 2,4-dichloroaniline (10.6 g), cupric oxide (0.8 g) and potassium carbonate (5.4 g) was stirred for 3 hours at 200° C. Ethyl acetate (100 ml) was added to the mixture, stirred and filtered. The filtrate was washed with water, dried and evaporated to dryness. The oil (15.5 g) was purified by column chromatography on silica gel (150 g) eluting with toluene to give an oil of 2-[3-(2,4-dichlorophenylamino)-4-nitrophenyl]-2-methyl-1,3-dioxolane (9.7 g).

Workup

stirringstirred
filtrationfiltered
washThe filtrate was washed with water
customdried
customevaporated to dryness
customThe oil (15.5 g) was purified by column chromatography on silica gel (150 g)
washeluting with toluene

Sources & evidence

ORD record: ord-712b1397105c49dfaec0dc1971e7beb1
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05034417

Reaction notes

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