8-Aminoquinoline → 5-bromoquinolin-8-amine

HRID 2090052Notes

Reaction equation

HRID 2090052 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:12]N1C(=O)CCC1=O>CC#N>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 67184N-bromobutanimide2×

Product 1

HCID 6138295-bromoquinolin-8-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 8-aminoquinoline (4.0 g, 28 mmol) in CH3CN (185 mL) was added N-bromosuccinimide (2.47 g, 13.9 mmol). After stirring for 15 minutes, a second portion of N-bromosuccinimide (2.71 g, 15.2 mmol) was added. After stirring for an additional 30 minutes, the mixture was concentrated. The residue was dissolved in EtOAc, then washed with water (2×100 mL) and saturated NaCl (aq) (100 mL). The organics were dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 10-15% EtOAc/hexanes to afford the title compound as a white solid: 1H NMR (500 MHz, CDCl3): δ 8.79 (dd, J=1.5, 4.1 Hz, 1H), 8.46 (dd, J=1.5, 8.5 Hz, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.52 (dd, J=4.1, 8.5 Hz, 1H), 6.83 (d, J=8.1 Hz, 1H); LC7: 2.48 min. (M+H) 225.

Workup

  1. stirringAfter stirring for an additional 30 minutes
  2. concentrationthe mixture was concentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water (2×100 mL) and saturated NaCl (aq) (100 mL)
  5. dry with materialThe organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 10-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-dcd643c531cc404aa4c7b0e30ce93188
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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