Sodium Hydroxide → (6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl)acetic acid

HRID 396421ノート

反応式

HRID 396421 の反応式
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH2:4][C:3]([OH:24])=[O:2])=[C:6]([C:15](=[O:23])[C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[NH:7]2)=[CH:12][CH:11]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 9906983HCID 9906983、化合物

生成物 1

HCID 9798374(6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl)acetic acid収率 91.3%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl[6-chloro-2-(4-chlorobenzoyl)-1H-indol-3-yl]acetate (Example 8, 1.80 g) and 2N aqueous NaOH (7.5 ml) in MeOH-THF (10 ml-10 ml) was stirred at 80° C. for 1 h. The mixture was cooled and concentrated. The residue was dissolved in water (150 ml) and washed with diethyl ether (50 ml). The aqueous layer was acidified with 2N aqueous HCl (10 ml), and extracted with ethyl acetate (100 ml×2). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), and concentrated. The residual solids were recrystalized from toluene to afford 1.58 g (91%) of the title compound.

後処理

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in water (150 ml)
  4. washwashed with diethyl ether (50 ml)
  5. extractionextracted with ethyl acetate (100 ml×2)
  6. washThe combined organic extracts were washed with brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residual solids were recrystalized from toluene

出典と根拠

ORDレコード
ord-e3f5642825574b27b621e57f37b843da
出典データセット
uspto-grants-2003_08
特許番号
US06608070B1

反応ノート

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