N-bromobutanimide → HCID 118075601, compound

HRID 1051569Notes

Reaction equation

HRID 1051569 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.[Br:19]N1C(=O)CCC1=O>C(#N)C>[Br:19][C:7]1[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][CH:2]([CH3:1])[CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 118075826HCID 118075826, compound

Product 1

HCID 118075601HCID 118075601, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A 50-mL round bottomed flask equipped with a magnetic stir bar and thermocouple was charged with rac-2-methyl-5-phenoxy-1,2,3,4-tetrahydroquinoline (0.574 g, 2.399 mmol) and acetonitrile (11.5 mL). The solution was cooled to 0° C., and N-bromosuccinimide (0.427 g, 2.399 mmol) was added in one portion. The solution turned yellow, and the internal temperature rose to 5° C. before falling back to 0° C. After 10 min, additional N-bromosuccinimide (0.021 g, 0.120 mmol) was added. After an additional 10 min, the reaction mixture was removed from the ice bath and concentrated under reduced pressure. The residue was then partitioned between ethyl acetate and 10% aqueous sodium carbonate solution. The layers were separated, and the ethyl acetate layer was washed with 5% aqueous sodium chloride solution (10 mL) and concentrated to a yellow oil (0.81 g). The crude product was purified by column chromatography on silica gel (eluting with 12:1 hexanes-ethyl acetate followed by 10:1 hexanes-ethyl acetate) to afford rac-6-bromo-2-methyl-5-phenoxy-1,2,3,4-tetrahydroquinoline (0.60, 79%) as a colorless syrup. MS (ESI, pos. ion) m/z 318, 320 [M+1].

Workup

  1. customA 50-mL round bottomed flask equipped with a magnetic stir bar
  2. customrose to 5° C.
  3. custombefore falling back to 0° C
  4. waitAfter an additional 10 min
  5. customthe reaction mixture was removed from the ice bath
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was then partitioned between ethyl acetate and 10% aqueous sodium carbonate solution
  8. customThe layers were separated
  9. washthe ethyl acetate layer was washed with 5% aqueous sodium chloride solution (10 mL)
  10. concentrationconcentrated to a yellow oil (0.81 g)
  11. customThe crude product was purified by column chromatography on silica gel (eluting with 12:1 hexanes-ethyl acetate followed by 10:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-12329f98cb3f4aa29fea4230815bd18b
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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