Hydrochloric Acid → 6-Bromo-4-cinnolinol

HRID 2307777

反応式

HRID 2307777 の反応式
[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[NH:11]C(=O)C)(=[O:3])[CH3:2].Cl.[N:16]([O-])=O.[Na+]>C1COCC1.O>[Br:10][C:8]1[CH:9]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:11][N:16]=[CH:2][C:1]2=[O:3]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 459291N-(2-acetyl-4-bromophenyl)acetamideHCID 23668193Sodium Nitrite

生成物 1

HCID 2709026-Bromo-4-cinnolinol収率 54.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of Example 34B (6.28 g, 24.4 mmol) in THF (75 mL) was treated with concentrated HCl (aq.) (15 mL) and water (15 mL), heated to reflux for 1 hour, and concentrated to remove the THF. The aqueous solution was treated with additional water (5 mL) and concentrated HCl (5 mL), cooled to 0° C., treated with a solution of NaNO2 (1.85 g, 26.84 mmol) in water (10 mL) in 5 portions, warmed to room temperature gradually over a 2-hour period, and stirred overnight at room temperature. The reaction was heated to reflux for 6 hours, and filtered. The solid was washed with water (50 mL) and diethyl ether (50 mL) and dried under vacuum to provide the desired product (3.0 g, 54%).

後処理

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. concentrationconcentrated
  4. customto remove the THF
  5. additionThe aqueous solution was treated with additional water (5 mL) and concentrated HCl (5 mL)
  6. temperaturewarmed to room temperature gradually over a 2-hour period
  7. temperatureThe reaction was heated
  8. temperatureto reflux for 6 hours
  9. filtrationfiltered
  10. washThe solid was washed with water (50 mL) and diethyl ether (50 mL)
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-e28fb059d7274dd78d539cae589bcf11
出典データセット
uspto-grants-2004_12
特許番号
US06831175B2

関連ノート

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