Acetone → 3-(4-fluorophenyl)-6-methyl-N-(propan-2-ylidene)-3,4-dihydroquinolin-1(2H)-amine

HRID 717761Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:18])[CH:15]=3)[N:10]([N:19]=O)[CH2:9]2)=[CH:4][CH:3]=1.[Cl-].[NH4+].O.[CH3:24][C:25]([CH3:27])=O>[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:18])[CH:15]=3)[N:10]([N:19]=[C:25]([CH3:27])[CH3:24])[CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 15 °C

Procedure

To a stirred solution of 3-(4-fluorophenyl)-6-methyl-1-nitroso-1,2,3,4-tetrahydroquinoline (0.28 g, 0.00103 mol) in acetone (15 mL) was added saturated ammonium chloride solution (0.6 mL), and water (0.6 mL) at RT. The resulting brown colored reaction mixture was cooled to 15° C. Zinc dust (0.269 g, 0.00414 mol) was added portionwise at the same temperature, and after the addition, the reaction mixture was stirred for 1 h at RT. The reaction was monitored by TLC. After completion, solvent was removed under reduced pressure and the residue extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, solvent was removed under reduced pressure to obtain product as a brown colored oil (0.27 g, 92.7% yield).

Workup

additionafter the addition
customAfter completion, solvent was removed under reduced pressure
extractionthe residue extracted with EtOAc (3×100 mL)
dry with materialThe organic layer was dried over anhydrous sodium sulfate, solvent
customwas removed under reduced pressure

Sources & evidence

ORD record: ord-3fb64ff3af674e98a78a6fe3dea274cf
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193728B2

Reaction notes

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