Ethyl Acetate → 6-Bromo-1,2,3,4-tetrahydroquinoline

HRID 1520152Notes

Reaction equation

HRID 1520152 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[NH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl>[Br:8][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:9][CH2:10][CH2:11][CH2:12]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 47150296-Bromo-1,2,3,4-tetrahydroquinolineYield 35%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

NBS (28 g, 158 mmol) was added to a solution of 1,2,3,4-tetrahydroquinoline (20 g, 150.16 mmol) in carbon tetrachloride (200 mL). The resulting solution was stirred for 3 h at 0° C., extracted with dichloromethane (3×50 mL) and concentrated in vacuo to give a residue, which was applied onto a silica gel column with 1% ethyl acetate in petroleum ether to give 6-bromo-1,2,3,4-tetrahydroquinoline as a yellow solid (11 g, 35%).

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. concentrationconcentrated in vacuo
  3. customto give a residue, which

Sources & evidence

ORD record
ord-73363feaa8f448679f88580056d01c35
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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