Hydrochloric Acid → 8-Nitro-(2,5-dimethyl-1H-indol-3-yl)quinoline

HRID 418446Notes

Reaction equation

HRID 418446 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH3:11])=[CH:6][CH:5]=2.[N+:12]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[C:20]2Cl)([O-:14])=[O:13].Cl.C(=O)([O-])O.[Na+]>CN1C(=O)CCC1.O1CCOCC1>[N+:12]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[C:22]([C:10]1[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:11])[CH:8]=3)[NH:3][C:2]=1[CH3:1])[CH:21]=[CH:20]2)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 709652,5-Dimethyl-1H-indoleHCID 516892Sodium BicarbonateHCID 6104404-Chloro-8-nitroquinoline

Product 1

HCID 666517798-Nitro-(2,5-dimethyl-1H-indol-3-yl)quinolineYield 85.6%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2,5-Dimethylindole (300 mg) and 8-nitro-4-chloroquinoline (430 mg) were suspended in NMP (10 ml) containing 4M HCl in dioxane (2 drops) and maintained under a nitrogen atmosphere. The reaction was heated to 120° C. with stirring for 8 hours. When cooled, the mixture was basified with saturated sodium hydrogen carbonate solution and extracted into ethyl acetate, dried (MgSO4) and evaporated under reduced pressure to give an oil. The oil was purified by flash column chromatography using 2:1 isohexane/ethyl acetate as eluent to give the sub-title compound (560 mg).

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. temperatureWhen cooled
  3. extractionextracted into ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give an oil
  7. customThe oil was purified by flash column chromatography

Sources & evidence

ORD record
ord-a3a638010abf439e81c9a94643e8af70
Source dataset
uspto-grants-2012_01
Patent number
US08093278B2

Reaction notes

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