Ethyl Acetate → 4-(4-Amino-2,3-dimethylphenoxy)-7-benzyloxy-6-cyanoquinoline

HRID 853595Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].[H-].[Na+].[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[C:32]#[N:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C>CS(C)=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:25]2[C:24]3[C:29](=[CH:30][C:21]([O:20][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:22]([C:32]#[N:33])[CH:23]=3)[N:28]=[CH:27][CH:26]=2)=[C:4]([CH3:9])[C:3]=1[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

4-Amino-2,3-xylenol (2.80 g) purchased from Tokyo Chemical Industries was dissolved in dimethylsulfoxide (15 ml), and after gradually adding sodium hydride (816 mg) at room temperature, the mixture was stirred for 20 minutes. 7-Benzyloxy-4-chloro-6-cyanoquinoline (3.0 g) was added, and the mixture was heated at 100° C. for 4 hours while stirring. After cooling to room temperature, the reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water, 1N aqueous sodium hydroxide and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained crude product was washed with ethyl acetate to obtain the title compound (1.72 g) as light brown crystals.

Workup

temperatureAfter cooling to room temperature
washthe organic layer was washed with water, 1N aqueous sodium hydroxide and saturated brine
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off
customthe obtained crude product
washwas washed with ethyl acetate

Sources & evidence

ORD record: ord-543e58c0238540b599e1365bd51cb283
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253286B2

Reaction notes

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