Water → 1-benzyl-5-nitro-2,3-dihydro-1H-indole

HRID 1359141

反応式

HRID 1359141 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)([O-:3])=[O:2].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:13]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 362195-Nitroindoline

生成物 1

HCID 98348711-benzyl-5-nitro-2,3-dihydro-1H-indole収率 58%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Under the presence of nitrogen, 5-nitroindolin (50 mg, 0.30 mmol) was dissolved in dimethylformamide (2 ml) at room temperature and benzyl bromide (0.04 ml. 0.34 mmol) and potassium carbonate (0.126 ml, 3.0 equivalent) were added and stirred at room temperature for 48 hours. After completing the reaction, water and ethyl acetate (respectively 5 ml) were added to separate layers, washed with brine, dried over anhydrous magnesium sulfate, and concentrated. Finally, the residue was purified through flash column chromatography (an eluent:ethyl acetate/n-hexane=1/4, v/v). As a result, the present compound (45 mg, productive yield 58%) was obtained.

後処理

  1. additionwere added
  2. customto separate layers
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customFinally, the residue was purified through flash column chromatography (an eluent
  7. customAs a result, the present compound (45 mg, productive yield 58%) was obtained

出典と根拠

ORDレコード
ord-d81cab0d5c0c41368ac4d3a883fc75fc
出典データセット
uspto-grants-2003_07
特許番号
US06599929B2

関連ノート

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