Dichloromethane → HCID 10382997, compound

HRID 1352495Notes

Reaction equation

HRID 1352495 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]([NH:12][CH2:13][C:14]#[CH:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].C(N([CH:30]([CH3:32])C)CC)(C)C.ClCCl.C(=O)([O-])[O-:37].[K+].[K+]>O1CCOCC1>[C:16]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]([N:12]([CH2:13][C:14]#[CH:15])[C:30](=[O:37])[CH3:32])[CH2:11][CH:2]1[CH3:1])(=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 22935713HCID 22935713, compound

Product 1

HCID 10382997HCID 10382997, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2-methyl-4-prop-2-ynylamino-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (0.06 g), diisopropyl ethyl amine (0.038 g) in dioxane (5 ml), anhydride acetic (0.2 g) was added under stirring. The mixture was heated under reflux over the night. After cooling dichloromethane and an aqueous solution of potassium carbonate were added. The organic layer was separated, and then dried over sodium sulfate. Organic solvent was removed under reduce pressure to give the crude compound (0.15 g). Purification by chromatography was performed with dichloromethane/methanol (99/1) as eluent to give the desired title compound (0.04 g, 58.8% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux over the night
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customOrganic solvent was removed
  6. customto give the crude compound (0.15 g)
  7. customPurification by chromatography

Sources & evidence

ORD record
ord-794b2bf971e7467ca02c7291e8721d69
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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