Water → 4-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1766015Notes

Reaction equation

HRID 1766015 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:19].O>C1COCC1>[N:1]1([C:18]([O:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:19])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 694601,2,3,4-TetrahydroquinolineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 178488194-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylateYield 108.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,2,3,4-Tetrahydroquinoline (1 ml, 7.97 mmol) was dissolved in THF (20 ml), and pyridine (1.58 ml, 15.93 mmol) was added thereto and cooled on ice. p-Nitrophenyl chloroformate (1.61 g, 7.97 mmol) was added to the reaction solution and stirred at room temperature for 4 hours, then water and a saturated saline solution were added, and the reaction solution was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure, whereby 2.57 g 4-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate was obtained as pale yellow solution.

Workup

  1. temperaturecooled on ice
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3851f739dee4ba0a10bb10ad5c0104f
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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