Hydrochloric Acid → HCID 10384843, compound

HRID 2354928Notes

Reaction equation

HRID 2354928 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:27](=[O:30])([O-])[OH:28].[Na+].[CH3:32]N1C(=O)CCC1>O1CCOCC1>[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]2[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:11])[CH:8]=2)[N:3]([CH2:32][C:27]([OH:28])=[O:30])[C:2]=1[CH3:1])([O-:14])=[O:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 709652,5-Dimethyl-1H-indoleHCID 516892Sodium BicarbonateHCID 6104404-Chloro-8-nitroquinoline

Product 1

HCID 10384843HCID 10384843, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneCatalyst

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-8b2e5f74cb764e728652827762685c8d
Source dataset
uspto-grants-2010_07
Patent number
US07754735B2

Reaction notes

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