Pyridine → HCID 118075637, compound

HRID 1051610Notes

Reaction equation

HRID 1051610 reaction equation
[Br:1][C:2]1[C:3]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH3:12])[CH2:6][CH2:5]2.N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27]>ClCCl>[Br:1][C:2]1[C:3]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:26](=[O:28])[CH3:27])[CH:7]([CH3:12])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chloride2×HCID 118075601HCID 118075601, compound

Product 1

HCID 118075637HCID 118075637, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of rac-6-bromo-2-methyl-5-phenoxy-1,2,3,4-tetrahydroquinoline (0.022 g, 0.069 mmol) in dichloromethane (1 mL), and pyridine (0.017 mL, 0.207 mmol) was cooled to 0° C. and treated with acetyl chloride (5.41 μL, 0.076 mmol). The reaction mixture was then stirred at rt. After 10 min, additional acetyl chloride (3.93 μL, 0.055 mmol) was added and stirring was continued at rt. After 75 min, the reaction mixture was diluted with dichloromethane and washed with 1 N aqueous hydrochloric acid solution (2×0.5 mL) and 5% aqueous sodium chloride solution (0.5 mL). The dichloromethane layer was concentrated to afford crude rac-1-(6-bromo-2-methyl-5-phenoxy-3,4-dihydroquinolin-1(2H)-yl)ethanone (0.024 g, 96%) as a nearly colorless gum that solidified upon standing. The crude product was used without further purification. MS (ESI, pos. ion) m/z 360, 362 [M+H]+.

Workup

  1. stirringstirring
  2. customwas continued at rt
  3. waitAfter 75 min
  4. washwashed with 1 N aqueous hydrochloric acid solution (2×0.5 mL) and 5% aqueous sodium chloride solution (0.5 mL)
  5. concentrationThe dichloromethane layer was concentrated

Sources & evidence

ORD record
ord-cfa3ac64411a491c93132d8e1e779e2d
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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