Water → HCID 68588682, compound

HRID 1183767Notes

Reaction equation

HRID 1183767 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]1[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:23][CH:22]=1.O>CN(C)C=O.C(OCC)C>[O:12]=[C:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([O:1][CH2:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])=[CH:23][CH:22]=3)=[CH:3][CH:4]=2)[NH:9]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27857587-Hydroxy-3,4-dihydrocarbostyrilHCID 11414578Tert-butyl 4-(bromomethyl)benzoate

Product 1

HCID 68588682HCID 68588682, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (2.015 g, 12.35 mmol) in anhydrous N,N-dimethylformamide (25 mL) was added potassium carbonate (1.880 g, 13.60 mmol) with stirring, and tert-butyl 4-(bromomethyl)benzoate (2.960 g, 10.83 mmol) in N,N-dimethylformamide (10 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes, then heated to 60° C. for 72 hours. The mixture was cooled, the solvent volume reduced to half under reduced pressure, and the residue poured slowly into water (100 mL) with stirring. Diethyl ether (5 mL) was added, the mixture sonicated, filtered, and the white solid thus obtained was washed with saturated sodium carbonate (60 mL), water (200 mL), diethyl ether (15 mL), and dried to afford tert-butyl 4-((2-oxo-1,2,3,4-tetrahydroquinolin-7-yloxy)methyl)benzoate (2.122 g, 6.00 mmol, 55%). LCMS mz 376.0 (M+Na), anal HPLC>92% in purity, 1H NMR (400 MHz; CDCl3) 8.00 (d, J=8.6 Hz, 1H); 7.55 (s, 2H); 7.45 (d, J=8.6 Hz, 2H); 7.05 (d, J=8.2 Hz, 1H); 6.57 (dd, J=8.4 and 2.5 Hz, 1H); 6.35 (d, J=2.3 Hz, 1H); 2.90 (m, 2H); 2.61 (m, 2H); 1.60 (s, 9H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. temperatureThe mixture was cooled
  3. stirringwith stirring
  4. customthe mixture sonicated
  5. filtrationfiltered
  6. customthe white solid thus obtained
  7. washwas washed with saturated sodium carbonate (60 mL), water (200 mL), diethyl ether (15 mL)
  8. customdried

Sources & evidence

ORD record
ord-230fcad8ea0043de804d5626321f0639
Source dataset
uspto-grants-2014_03
Patent number
US08664379B2

Reaction notes

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