Triethylamine → 3-Chloro-4-(6-hydroxyquinolin-2-yl)benzonitrile

HRID 2280454Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[N:12]=1)[C:5]([NH2:7])=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.CCN(CC)CC>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[N:12]=1)[C:5]#[N:7]

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of crude 3-chloro-4-(6-hydroxyquinolin-2-yl)benzamide (360 mg), TFAA (505 mg, 2.40 mmol) and Et3N (364 mg, 3.62 mmol) in DCM (20 mL) was stirred at 30° C. overnight. The resulting mixture was suspended in water (50 mL) and extracted with EtOAc (50 mL×3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc=10/1) to give the product (250 mg, 3-step yield 67%) as a solid.

Workup

extractionextracted with EtOAc (50 mL×3)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (PE/EtOAc=10/1)
customto give the product (250 mg, 3-step yield 67%) as a solid

Sources & evidence

ORD record: ord-2e58f296e20148bd82f16d8390c505eb
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139528B2

Reaction notes

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