Pyridine → HCID 118075402, compound

HRID 1051612Notes

Reaction equation

HRID 1051612 reaction equation
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:3]1.N1C=CC=CC=1.[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]1[C:25](=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 118075826HCID 118075826, compound

Product 1

HCID 118075402HCID 118075402, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A glass, screw-cap vial equipped with a magnetic stir bar was charged with a solution of rac-2-methyl-5-phenoxy-1,2,3,4-tetrahydroquinoline (0.050 g, 0.21 mmol) in dichloromethane (1 mL) and pyridine (0.051 mL, 0.630 mmol). The solution was cooled to 0° C. and acetyl chloride (0.015 mL, 0.210 mmol) was added. The ice bath was removed and the reaction mixture stirred at rt. After 10 min, the reaction mixture was diluted with dichloromethane and washed with 1 N aqueous hydrochloric acid solution (2×1 mL) followed by 5% aqueous sodium chloride solution (1 mL). The organic layer was concentrated to a yellow oil, which crystallized upon standing. The crude product was purified by preparative thin layer chromatography (1×1000 micron plate, eluting with 2:1 hexanes-ethyl acetate) to yield 1-(2-methyl-5-phenoxy-3,4-dihydroquinolin-1(2H)-yl)ethanone (0.0189 g, 32%) as a nearly colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.13 (d, J=6.60 Hz, 3 H), 1.36-1.55 (m, 1H), 2.11-2.27 (m, 4H), 2.36 (br s, 1H), 2.85 (dt, J=16.04, 6.09 Hz, 1H), 4.88 (br s, 1H), 6.76 (d, J=8.80 Hz, 1H), 6.89-6.96 (m, 2H), 6.96-7.04 (m, 1H), 7.04-7.11 (m, 1H), 7.12-7.19 (m, 1H), 7.29-7.37 (m, 2H). MS (ESI, pos. ion) m/z 282 [M+H]+.

Workup

  1. customA glass, screw-cap vial
  2. customequipped with a magnetic stir bar
  3. customThe ice bath was removed
  4. additionthe reaction mixture was diluted with dichloromethane
  5. washwashed with 1 N aqueous hydrochloric acid solution (2×1 mL)
  6. concentrationThe organic layer was concentrated to a yellow oil, which
  7. customcrystallized
  8. customThe crude product was purified by preparative thin layer chromatography (1×1000 micron plate, eluting with 2:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-1b97c7c57a3548cf9416dcabd1092a00
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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