Hydrochloric Acid → 2-(2-fluoro-6-methoxyphenyl)-7-methylquinazolin-4(3H)-one

HRID 1692997ノート

反応式

HRID 1692997 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[NH:10][C:11](=O)[C:12]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=1[F:20])#[N:2].[OH-:22].[Na+].OO.Cl>C(O)C>[F:20][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([O:18][CH3:19])[C:12]=1[C:11]1[NH:2][C:1](=[O:22])[C:3]2[C:4](=[CH:5][C:6]([CH3:9])=[CH:7][CH:8]=2)[N:10]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide4 回HCID 14798Sodium Hydroxide3 回HCID 58683864N-(2-cyano-5-methylphenyl)-2-fluoro-6-methoxybenzamide

生成物 1

HCID 1361215392-(2-fluoro-6-methoxyphenyl)-7-methylquinazolin-4(3H)-one収率 89%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of N-(2-cyano-5-methylphenyl)-2-fluoro-6-methoxybenzamide (31.5 g, 111 mmol) in ethanol (626 mL) was added 6 M aqueous NaOH solution (205 mL). After 10 minutes, 30% aqueous H2O2 (60 mL) was added, forming a slurry. The reaction was heated to reflux for 18 h and cooled to room temperature. NaOH (22.2 g, 0.56 mol) and 30% aqueous H2O2 (26 mL) were added, and the reaction was heated to reflux for six hours. The reaction cooled to room temperature, 30% aqueous H2O2 (45 mL) was added, and the reaction was heated to reflux for 18 h. The reaction was cooled to room temperature, NaOH (10 g, 0.25 mol) and 30% aqueous H2O2 (70 mL) were added, and the reaction was heated to reflux for six hours. The reaction was cooled to room temperature and poured over ice (800 mL). The pH was adjusted to 3-4 by addition of conc. HCl solution, and the precipitated off-white solid was filtered and washed with water (3×40 mL). The solid was dried under vacuum to provide 2-(2-fluoro-6-methoxy-phenyl)-7-methyl-3H-quinazolin-4-one (28 g, 89%).

後処理

  1. customforming a slurry
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 18 h
  4. temperaturethe reaction was heated
  5. temperatureto reflux for six hours
  6. temperatureThe reaction cooled to room temperature
  7. temperaturethe reaction was heated
  8. temperatureto reflux for 18 h
  9. temperatureThe reaction was cooled to room temperature
  10. temperaturethe reaction was heated
  11. temperatureto reflux for six hours
  12. temperatureThe reaction was cooled to room temperature
  13. filtrationthe precipitated off-white solid was filtered
  14. washwashed with water (3×40 mL)
  15. customThe solid was dried under vacuum

出典と根拠

ORDレコード
ord-30fa4dc9bdc84fb2ba79925a8f72ecc2
出典データセット
uspto-grants-2012_04
特許番号
US08158637B2

反応ノート

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