Benzyl Bromide → Phenyl 7-benzyloxy-4-oxo-1,4-dihydro-6-quinolinecarboxylate

HRID 388035Notes

Reaction equation

HRID 388035 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH:25]=[CH:24][C:14]([C:15]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])=[C:13]([OH:26])[CH:12]=2)C(=O)O1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C.O1CCCC1>CN(C)C=O.C(O)C.CCCCCC.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.C(OCC)C.O>[CH2:29]([O:26][C:13]1[CH:12]=[C:11]2[C:25]([C:6](=[O:8])[CH:5]=[CH:9][NH:10]2)=[CH:24][C:14]=1[C:15]([O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:16])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

11

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21868444Ether tetrahydrofuranHCID 22936474Phenyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-hydroxybenzoate

Product 1

HCID 22936353Phenyl 7-benzyloxy-4-oxo-1,4-dihydro-6-quinolinecarboxylateYield 10,766.7%

Reagents, catalysts & solvents 6

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

Phenyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-hydroxybenzoate (11.5 g, 0.030 mmol), benzyl bromide (5.64 g, 0.033 mmol) and potassium carbonate (4.56 g, 0.033 mmol) were stirred in dimethylformamide (45 ml) at 80° C. for 3 hours. The reaction solution was distributed between a diethyl ether-tetrahydrofuran mixed solvent and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and the drying agent was filtered out and the filtrate distilled off under reduced pressure. The obtained crude product was suspended in ethanol, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and blow-dried to obtain white crystals. The crystals were then heated and stirred for 1 hour in Dowtherm A (50 ml) at 200° C. After allowing the reaction solution to cool to room temperature, diethyl ether (25 ml) was added and the mixture was further stirred overnight. The precipitated crystals were filtered out, washed with diethyl ether and blow-dried to obtain the title compound (1.20 g, 3.23 mmol, 11%) as white crystals.

Workup

  1. washthe organic layer was washed with water and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered out
  4. distillationthe filtrate distilled off under reduced pressure
  5. customThe obtained crude product
  6. filtrationthe crystals were filtered out
  7. washwashed with hexane
  8. customblow-dried
  9. customto obtain white crystals
  10. temperatureThe crystals were then heated
  11. filtrationThe precipitated crystals were filtered out
  12. washwashed with diethyl ether
  13. customblow-dried

Sources & evidence

ORD record
ord-c1d35869d82c416bae3219b22b545277
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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