Potassium Carbonate → 1-(2-(Dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one

HRID 1922430Notes

Reaction equation

HRID 1922430 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.Cl.Cl[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[F:1])[CH2:7][CH2:8][C:9]1=[O:12]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 674929281-(2-(Dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one

Procedure

8-Fluoro-3,4-dihydroquinolin-2(1H)-one (2.31 g, 13.98 mmol), 2-chloro-N,N-dimethylethanamine hydrochloride (4.03 g, 27.9 mmol) and potassium carbonate (11.78 g, 85.3 mmol) were combined in a round bottom flask containing a stirbar. The flask was purged with argon and DMF was added. The white suspension was stirred overnight at room temperature. The mixture was then diluted with ethyl acetate and washed with water (5×), then brine (2×). The organic phase was then dried, filtered and concentrated, then chromatographed on silica gel using EtOAc eluent. Yield: 2.86 g, 86%. 1H NMR 7.0 Hz), 4.09 (t, 2H, J=7.0 Hz), 6.98 (m, 3H). ESI-MS: 237 (MH+, 29), 192 (100). (CDCl3) δ 2.24, (s, 6H), 2.51 (t, 2H, J=7.0 Hz), 2.59 (t, 2H, J=7.0 Hz), 2.87 (t, 2H, J=

Workup

  1. additioncontaining a stirbar
  2. customThe flask was purged with argon and DMF
  3. additionwas added
  4. additionThe mixture was then diluted with ethyl acetate
  5. washwashed with water (5×)
  6. customThe organic phase was then dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel

Sources & evidence

ORD record
ord-d0b9fee18664489ba7c2a3d95a054d57
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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