1-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one → 1-Ethyl-5-aminoindoline

HRID 507354

反応式

HRID 507354 の反応式
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)[CH3:2]

参加物

4

反応物 2

HCID 2925071-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 230087101-Ethyl-5-aminoindoline収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 1-acetyl-5-aminoindoline (130 mg, 0.74 mmol) in anhydrous THF (10 mL) was added LiAlH4 (42 mg, 1.11 mmol). The mixture was stirred at rt for 6 h, quenched with saturated NH4Cl and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give a purple residue (80 mg, 67%) that was used without further purification. 1H NMR (270 MHz, DMSO): δ 6.56 (1H, s, ArH), 6.47 (1H, d broad, J=8.1 Hz, ArH), 6.37 (1H, d, J=8.0 Hz, ArH), 3.29 (2H, s, NH2), 3.20 (2H, t, J=7.6 Hz, CH2), 3.02 (2H, q, J=6.9 Hz, CH2), 2.86 (2H, t, J=7.6 Hz, CH2), 1.17 (3H, t, J=6.9 Hz, CH3).

後処理

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4d9553978bd54320a331925c76e285c2
出典データセット
uspto-grants-2010_08
特許番号
US07786152B2

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