Hydrochloric Acid → 2-Amino-2-(4-fluorophenyl)-1-quinolin-8-ylethanol

HRID 1170396Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21]C(=O)OC(C)(C)C)[CH:9]([OH:20])[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)=[CH:4][CH:3]=1.Cl>C(Cl)Cl.O1CCOCC1>[NH2:21][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:9]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)[OH:20]

Participants

Conditions

Temperature: 0 °C

Procedure

2.78 g (7.27 mmol) of tert-butyl [1-(4-fluorophenyl)-2-hydroxy-2-quinolin-8-ylethyl]carbamate were dissolved in 75 ml of methylene chloride and cooled to 0° C. 18 ml of an HCl solution (4N) in dioxane were added, and the mixture was stirred at 0° C. for 20 minutes and allowed to reach room temperature overnight. The reaction mixture was concentrated in vacuo, and the residue was treated with diisopropyl ether. Filtration was followed by washing with diisopropyl ether and pentane and drying in vacuo. 2.75 g of 2-amino-2-(4-fluorophenyl)-1-quinolin-8-ylethanol were obtained as hydrochloride (diastereoisomer mixture: 85/15) as a pale yellow very hygroscopic powder (yield: quantitative). The substance was used without further purification for the next stage.

Workup

waitto reach room temperature overnight
concentrationThe reaction mixture was concentrated in vacuo
additionthe residue was treated with diisopropyl ether
filtrationFiltration
washby washing with diisopropyl ether and pentane
customdrying in vacuo

Sources & evidence

ORD record: ord-d383ac7f59b4490b8dd07c94ae82bdf8
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825264B2

Reaction notes

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