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

HRID 1433696
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HRID 1433696 반응식
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
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참가 물질

11

반응물 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

생성물 1

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

시약·촉매·용매 6

HCID 702
Ethanol
용매
HCID 962Water용매
HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매
HCID 8058Hexane용매
HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)용매

실험 절차

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 brine 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.

후처리

  1. washthe organic layer was washed with water and saturated brine
  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

출처 및 근거

ORD 기록
ord-6c6cd9f53a1346119146fd4124c2c396
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612092B2

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