N-bromobutanimide → (S)-1-(6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 1051563Notes

Reaction equation

HRID 1051563 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C@H:6]([CH3:15])[N:7]2[C:12](=[O:14])[CH3:13].[Br:16]N1C(=O)CCC1=O>C(#N)C>[Br:16][C:11]1[C:2]([OH:1])=[C:3]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:12](=[O:14])[CH3:13])[C@@H:6]([CH3:15])[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118075867(S)-1-(5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

Product 1

HCID 118075679(S)-1-(6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanoneYield 82.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (S)-1-(5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1.2 g, 5.85 mmol) in acetonitrile (24 mL) was cooled to 0° C. and treated with N-bromosuccinimide (1.041 g, 5.85 mmol) in one portion. The solution turned dark yellow-orange in color initially, then faded to a pale orange color over the next 10-15 min. After 30 min, the solution was concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 8:1 dichloromethane-ethyl acetate followed by 7:1 dichloromethane-ethyl acetate) to afford (S)-1-(6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1.37 g, 82%). MS (ESI, pos. ion) m/z 284, 286 [M+1]+.

Workup

  1. customfaded to a pale orange color over the next 10-15 min
  2. concentrationthe solution was concentrated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel (eluting with 8:1 dichloromethane-ethyl acetate followed by 7:1 dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-9f480147b86b4fb8a5e18a8b9e215f84
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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