Sodium Iodide → Heptyl-Carbamic Acid quinolin-6-yl ester

HRID 1441927Notes

Reaction equation

HRID 1441927 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]([N:19]=[C:20]=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:20](=[O:21])[NH:19][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 113746-HydroxyquinolineHCID 11430Potassium CarbonateHCID 138341n-Heptyl isocyanate

Product 1

HCID 11558303Heptyl-Carbamic Acid quinolin-6-yl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of quinolin-6-ol (0.58 g., 4 mmol), heptyl isocyanate (0.77 ml, 4.8 mmol), potassium carbonate (0.56 g., 4 mmol) and sodium iodide (0.60 g., 4 mmol) in dry dimethylformamide (2 ml) was stirred at 50° C. for 12 hours. The reaction mixture was diluted with water (5 ml), extracted with ethyl acetate (2×5 ml) and chromatographed on silica gel with chloroform as an eluant to give (1b), yield: 0.50 g. (43.7%).

Workup

  1. extractionextracted with ethyl acetate (2×5 ml)
  2. customchromatographed on silica gel with chloroform as an eluant

Sources & evidence

ORD record
ord-8bbddba87ea74e20b5cd35f275825f75
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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