Dichloromethane → cis-4-(Acetyl-phenylamino)-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester

HRID 1352488Notes

Reaction equation

HRID 1352488 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][C@@H:12]1[CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH:35]([CH3:37])C)CC)(C)C.ClCCl.C(=O)([O-])[O-:42].[K+].[K+]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([N:21]([C:35](=[O:42])[CH3:37])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][C@@H:12]1[CH3:28])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 12093188cis-2-Methyl-4-phenylamino-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester

Product 1

HCID 12093189cis-4-(Acetyl-phenylamino)-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of cis-2-methyl-4-phenylamino-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (5.3 g), diisopropyl ethyl amine (2.73 g) in dioxane (31 ml), anhydride acetic (7.26 g) was added under stirring. The mixture was heated under reflux over 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 (18 g). The desired compound (3.8 g, 64% yield) was obtained after purification by flash chromatography on silica gel with cyclohexane/ethyl acetate (80/20) as eluent and then cyclohexane/ethyl acetate (50/50).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux over night
  3. temperatureAfter cooling
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customOrganic solvent was removed
  7. customto give the crude compound (18 g)

Sources & evidence

ORD record
ord-4072c7e77be0403e82a36a5059fec4ae
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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