Hydrochloric Acid → 3-(2-(7-Chloroquinolin-2-yl)cyclopropyl)phenol

HRID 1088471Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]3[CH2:14][CH:13]3[C:15]3[CH:16]=[C:17]([O:21]C)[CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].C(S)C.Cl>C(Cl)Cl.C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]3[CH2:14][CH:13]3[C:15]3[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To the cyclopropylanisole (from Step 2) (1.478 g, 4.77 mmoles) in 20 mL CH2Cl2 at -10° C. was added AlCl3 (1.915 g, 3 eg.) and ethanethiol (1.2 mL, 3.3 eg.). The temperature was raised to 0° C. for 2 hours. Then 10% HCl and THF: EtOAc (1:1) were added and the mixture was stirred and heated until the resulting gum was solubilized. After separation of the phases and extractions with THF:EtOAc (1:1), flash chromatography using 5% EtOAc in toluene yielded the title phenol.

Workup

temperatureheated until the resulting gum
customAfter separation of the phases and extractions with THF:EtOAc (1:1), flash chromatography

Sources & evidence

ORD record: ord-18322f49d8ab44d6a2a48ea3d7203243
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04962203

Reaction notes

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