N-bromobutanimide → 6-Bromo-1,2,3,4-tetrahydroquinoline

HRID 2353462Notes

Reaction equation

HRID 2353462 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Br:11]N1C(=O)CCC1=O>C(#N)C.CCOCC>[Br:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][CH2:4]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 47150296-Bromo-1,2,3,4-tetrahydroquinolineYield 58%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

1,2,3,4-tetrahydroquinoline (1.7 g, 12.8 mmol) was dissolved in acetonitrile (25 mL) and cooled to 0° C. N-Bromosuccinimide (2.16 g, 12.2 mmol) was added in 4 portions over 30 minutes and the mixture was stirred for 3 hours. The mixture was diluted with ether and washed with sodium bisulfite, water, brine, dried over anhydrous magnesium sulfate, and concentrated. Purification via Isco chromatography (the Redisep® column, silica, gradient 5%-30% ethyl acetate in hexane) afforded 6-bromo-1,2,3,4-tetrahydroquinoline (1.5 g). MS (ES) m/z 211.8; HPLC purity 100.0% at 210-370 nm, 10.9 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammonium formate buffer pH=3.5 acetonitrile+MeOH) for 10 minutes, hold 4 minutes.

Workup

  1. washwashed with sodium bisulfite, water, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customPurification via Isco chromatography (the Redisep® column, silica, gradient 5%-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5fc5394c87944312bee1a3242e710031
Source dataset
uspto-grants-2010_07
Patent number
US07750038B2

Reaction notes

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