Diethyl Ether → 4,7-dichloro-1-pentyl-1H-indole-2,3-dione

HRID 1259616ノート

反応式

HRID 1259616 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:5]=1[C:6](=[O:15])[C:7](=[O:14])[NH:8]2.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(OCC)C>CN(C)C=O>[Cl:3][C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:5]=1[C:6](=[O:15])[C:7](=[O:14])[N:8]2[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 27347934,7-Dichloroisatin

生成物 1

HCID 666426684,7-dichloro-1-pentyl-1H-indole-2,3-dione収率 98%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

To a mixture of sodium hydride (0.17 g, 6.94 mmol, 60% dispersion in mineral oil) in anhydrous N,N-dimethylformamide (5.00 mL) was added a solution of 4,7-dichloro-1H-indole-2,3-dione (1.00 g, 4.60 mmol) in N,N-dimethylformamide (5.00 mL) at 0° C. The brown reaction mixture was stirred for 0.5 h followed by the addition of a solution of 1-bromopentane (0.84 g, 5.55 mmol) in anhydrous N,N-dimethylformamide (5.00 mL). The reaction mixture was stirred at ambient temperature for 16 h and poured into wet ethyl ether (30.0 mL). After the organic layer was separated, it was washed with water (2×20.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The gummy residue was dried under vacuum and the solid was triturated with ether to give the title compound (0.98 g, 98%): MS (ES+) m/z 286.2 (M+1).

後処理

  1. stirringThe reaction mixture was stirred at ambient temperature for 16 h
  2. customAfter the organic layer was separated
  3. washit was washed with water (2×20.0 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customThe gummy residue was dried under vacuum
  8. customthe solid was triturated with ether

出典と根拠

ORDレコード
ord-c7905727e3744155bc0447757dd6feec
出典データセット
uspto-grants-2013_06
特許番号
US08466188B2

反応ノート

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