ethyl quinoline-3-carboxylate → Ethyl 1,2,3,4-tetrahydroquinoline-3-carboxylate

HRID 253114Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:2]=1>C(O)(=O)C>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

Borane-pyridine complex (8 M, 292 mL, 2.34 mmol) was added to a solution of Ethyl quinoline-3-carboxylate (235 mg, 1.17 mmol) in acetic acid (10 mL). The solution was stirred at 25° C. for 20 h. The reaction mixture was concentrated in vacuo, basified with 1 M sodium carbonate (30 mL), and the product was extracted with dichloromethane (3×35 mL). The organic layers were dried over sodium sulfate and concentrated. Purification of the product by flash column chromatography (10% to 20% EtOAc/hexane) afforded the title compound (239 mg, 1.15 mmol). MS m/z: 206 (M+1).

Workup

concentrationThe reaction mixture was concentrated in vacuo
extractionthe product was extracted with dichloromethane (3×35 mL)
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated
customPurification of the product by flash column chromatography (10% to 20% EtOAc/hexane)

Sources & evidence

ORD record: ord-fe50d86f25214fa491b2f1f3f992f04c
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872009B2

Reaction notes

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