Chlorosuccinimide → 5-Bromo-7-chloro-8-quinolinamine

HRID 2090053Notes

Reaction equation

HRID 2090053 reaction equation
[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.[Cl:13]N1C(=O)CCC1=O>CC#N>[NH2:1][C:2]1[C:3]([Cl:13])=[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 31398ChlorosuccinimideHCID 6138295-bromoquinolin-8-amine

Product 1

HCID 583494345-Bromo-7-chloro-8-quinolinamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 8-amino-5-bromoquinoline (440 mg, 1.97 mmol) in CH3CN (39 mL) was added N-chlorosuccinimide (250 mg, 1.87 mmol). The mixture was stirred at 75° C. until no further conversion of the starting material was observed by LC/MS and TLC analysis. The mixture was allowed to cool to room temperature then concentrated. The residue was dissolved in EtOAc, then washed with water (2×50 mL) then saturated NaCl (aq) (50 mL). The organic phase was dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 15% EtOAc/hexanes to afford the title compound as a solid: 1H NMR (500 MHz, CDCl3): δ 8.81 (dd, J=1.4, 4.1 Hz, 1H) 8.43 (dd, J=1.4, 8.5 Hz, 1H), 7.71 (s, 1H), 7.51 (dd, J=4.1, 8.5 Hz, 1H); LC6: 4.27 min. (M+H) 259.

Workup

  1. temperatureto cool to room temperature
  2. concentrationthen concentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water (2×50 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-e20a1744a7db48f08c9ff7ff001e5665
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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