Hydrochloric Acid → (S)-1-(5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 1051562Notes

Reaction equation

COC[O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C@H:9]([CH3:18])[N:10]2[C:15](=[O:17])[CH3:16].Cl>CO>[OH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C@H:9]([CH3:18])[N:10]2[C:15](=[O:17])[CH3:16]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of (S)-1-(5-(methoxymethoxy)-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1.6 g, 6.42 mmol) in methanol (16 mL) was treated with concentrated hydrochloric acid (1.0 mL, 12.8 mmol) at rt. The solution was heated to 50° C. for 90 min. Heating was discontinued, and the solution was allowed to slowly cool to room temperature overnight. Methanol was removed under reduced pressure and the residue was partitioned between dichloromethane and water. The aqueous layer was separated and extracted with dichloromethane. The combined organic extracts were concentrated under reduced pressure. The residue was dissolved in acetonitrile (ca. 20-30 mL), and then concentrated under reduced pressure to afford (S)-1-(5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1.23 g, 93%) as an off-white to tan solid. MS (ESI, pos. ion) m/z 206 [M+1]+.

Workup

temperatureHeating
temperatureto slowly cool to room temperature overnight
customMethanol was removed under reduced pressure
customthe residue was partitioned between dichloromethane and water
customThe aqueous layer was separated
extractionextracted with dichloromethane
concentrationThe combined organic extracts were concentrated under reduced pressure
dissolutionThe residue was dissolved in acetonitrile (ca. 20-30 mL)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9d52771290294234a65684f4f059e884
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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