Diphenyl Ether → 4-(3-Chloro-4-methoxy-benzylamino)-quinoline-6-carbonitrile

HRID 2308232Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=3)[N:15]=[CH:14][C:13]=2C(O)=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 240 °C

Procedure

To 2.16 g (5.87 mmol) 4-[[(3-chloro-4-methoxyphenyl)-methyl]amino]-6-cyano-3-quinolinecarboxylic acid was added 50 mL diphenyl ether (Aldrich), and nitrogen was vigorously bubbled through this mixture for 20 minutes. The resulting mixture was then heated to 240° C. under nitrogen for 30 minutes. During the course of the reaction, the dispersed starting material slowly dissolved, and gas evolution was observed. The resulting solution was poured into 200 mL hexane, and a precipitated solid was filtered to yield 1.43 g (4.42 mmol, 75% yield) of the title compound as a off-white solid: LC/MS: M/Z 324 (M+H) observed, 96% purity; mp: decomposed 227-230° C. LC: 2.84′.

Workup

customwas vigorously bubbled through this mixture for 20 minutes
customDuring the course of the reaction
dissolutionslowly dissolved
filtrationa precipitated solid was filtered

Sources & evidence

ORD record: ord-90e447814412474a89a5bd0046cde9ff
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06835737B2

Reaction notes

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