Cyclopropanecarbonyl chloride → 2-Cyclopropylcarbonyl-1-methyl-1H-imidazo[4,5-c]quinoline

HRID 2165544Notes

Reaction equation

HRID 2165544 reaction equation
[CH3:1][N:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:4]=[CH:3]1.C([Li])CCC.[CH:20]1([C:23](Cl)=[O:24])[CH2:22][CH2:21]1>C1COCC1.CCCCCC>[CH:20]1([C:23]([C:3]2[N:2]([CH3:1])[C:14]3[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:7]=[CH:6][C:5]=3[N:4]=2)=[O:24])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 139583741H-Imidazo[4,5-c]quinoline, 1-methyl-HCID 178418339Butyllithium

Product 1

HCID 146218102-Cyclopropylcarbonyl-1-methyl-1H-imidazo[4,5-c]quinolineYield 36.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In the same manner as in Ex. 1, to a solution containing 550 mg of 1-methyl-1H-imidazo[4,5-c]quinoline (II-2) in 25 ml of THF and a mixture of 2.2 ml of 1.6M solution of n-butyl lithium in hexane-2 ml of THF was added 0.75 g of cyclopropanecarbonyl chloride. The reaction mixture was gradually warmed to room temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and aqueous ammonia. The organic layer was washed with water and brine, and then dried. The ethyl acetate was removed by evaporation, and the residue was chromatographed on a column of silica gel for purification. The fraction eluted with ethyl acetate was concentrated and the residue was crystallized from n-hexane to give 275 mg (yield: 36%) of the titled compound (Ia-1). This was recrystallized from ethyl acetate n-hexane to give colorless crystals melting at 156°~158° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and aqueous ammonia
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. customThe ethyl acetate was removed by evaporation
  6. customthe residue was chromatographed on a column of silica gel for purification
  7. washThe fraction eluted with ethyl acetate
  8. concentrationwas concentrated
  9. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-e1a5f66a1bc844b484a28695a3e487c6
Source dataset
uspto-grants-1990_07
Patent number
US04940714

Reaction notes

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