Sulfuric Acid → 7-(Benzyloxy)-6-methoxyquinolin-4-ol

HRID 1008322Notes

Reaction equation

HRID 1008322 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([O:16][CH3:17])=[CH:4][C:3]=1[C:18](=[O:20])[CH3:19].C[O-].[Na+].[CH:24](OCC)=O.S(=O)(=O)(O)O>O1CCCC1.O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]2[C:3]([C:18](=[O:20])[CH:19]=[CH:24][NH:1]2)=[CH:4][C:5]=1[O:16][CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8025Ethyl formateHCID 10942334Sodium MethoxideHCID 226671471-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

Product 1

HCID 226465797-(Benzyloxy)-6-methoxyquinolin-4-olYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1-[2-Amino-4-(benzyloxy)-5-methoxyphenyl]-1-ethanone (24.95 g) was dissolved in tetrahydrofuran (450 ml), and sodium methoxide (24.87 g) was added to the solution. The mixture was stirred at room temperature for one hr. Ethyl formate (37.07 ml) was then added thereto, and the mixture was stirred at room temperature for 2 hr. Water (150 ml) was then added thereto, and the mixture was stirred overnight. The reaction solution was adjusted to pH 4 by the addition of concentrated sulfuric acid at 0° C. Water was added thereto, and the mixture was extracted with chloroform. The chloroform layer was dried over sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/methanol (10/1) to give 17.16 g (yield 66%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. stirringthe mixture was stirred overnight
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe chloroform layer was dried over sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by chromatography on silica gel by development with chloroform/methanol (10/1)

Sources & evidence

ORD record
ord-08abb0a7001c42cfa9de11be440039c4
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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