Acetaldehyde → 5,7-dichloro-3-methyl-3-(4-ethylamino-phenyl)-1H-quinoline-2,4-dione

HRID 735264Notes

Reaction equation

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

Participants

Reactant 3

HCID 177Acetaldehyde

HCID 5360545Sodium

HCID 115735593-(4-amino-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

Product 1

HCID 115741135,7-dichloro-3-methyl-3-(4-ethylamino-phenyl)-1H-quinoline-2,4-dioneYield 4%

Procedure

The objective compound was prepared by the same procedure for the example 39 and 40, using a 3-(4-amino-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione (235 mg, 0.70 mmol), acetaldehyde (148 mL, 2.10 mmol), and sodium borocyanohydride (44 mg, 0.70 mmol). After normal workup, The residue was purified by a flash column chromatography (n-hexane:EtOAc=8:1) to give two separable objective chemical compounds of 5,7-dichloro-3-methyl-3-(4-ethylamino-phenyl)-1H-quinoline-2,4-dione (10 mg, 4%, yellow solid) and 5,7-dichloro-3-(4-diethylamino-phenyl)-3-methyl-1H-quinoline-2,4-dione (220 mg, 87%, pale yellow solid:

Workup

customThe objective compound was prepared by the same procedure for the example 39 and 40
customAfter normal workup, The residue was purified by a flash column chromatography (n-hexane:EtOAc=8:1)

Sources & evidence

ORD record: ord-2bebf1c453574864a4bbc6e004ddebb4
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592457B2

Reaction notes

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