Sodium Hydroxide → 6-Bromo-4-chlorocinnoline

HRID 2307778

反応式

HRID 2307778 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[CH:6][C:5]2=O.[OH-].[Na+].O=P(Cl)(Cl)[Cl:17]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[N:7][CH:6]=[C:5]2[Cl:17]

参加物

4

反応物 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 2709026-Bromo-4-cinnolinol

生成物 1

HCID 124480786-Bromo-4-chlorocinnoline収率 43%

反応条件

温度
0 °C

実験手順

A solution of Example 34C (0.4 g, 1.8 mmol) in POCl3 (2.5 mL) was heated to 100° C. for 2 hours, and poured slowly onto ice. The aqueous layer was cooled to 0° C. and adjusted to pH 5-7 with 50% NaOH. The aqueous layer was extracted with ethyl acetate (2×50 mL), and the combined organic layers were concentrated. The residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate to provide the desired product (0.190 g, 43%).

後処理

  1. additionpoured slowly onto ice
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. concentrationthe combined organic layers were concentrated
  4. customThe residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-8e45b3c3aee24d2191646d7def1850e8
出典データセット
uspto-grants-2004_12
特許番号
US06831175B2

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