Diisopropylethylamine → HCID 68727240, compound

HRID 408656Notes

Reaction equation

HRID 408656 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1.[C:16]1([CH:22]2[CH2:26][CH2:25][NH:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C>C(OCCO)C.O>[CH3:15][C:4]1[CH:3]=[C:2]([N:24]2[CH2:25][CH2:26][CH:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23]2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 31467433-PhenylpyrrolidineHCID 50849494-Chloro-2-methyl-6-nitroquinoline

Product 1

HCID 68727240HCID 68727240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

4-Chloro-2-methyl-6-nitroquinoline (0.2 g), 3-phenylpyrrolidine (0.14 g) and diisopropyl-ethylamine (0.27 mL) in 2-ethoxyethanol (4 mL) was heated in a microwave to 200° C. for 15 minutes. The reaction mixture was diluted with water and extracted with dichloromethane, washed with water, dried (Na2SO4), filtered and evaporated to give a yellow oil. The residue was purified by chromatography on silica, eluting with a mixture of dichloromethane, ethanol and ammonia (200:8:1). The desired fractions were concentrated to give the title compound as an orange oil.

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a yellow oil
  7. customThe residue was purified by chromatography on silica
  8. washeluting with a mixture of dichloromethane, ethanol and ammonia (200:8:1)
  9. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-4ad53941504043fda5a49d00343054c2
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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