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

HRID 970038Notes

Reaction equation

HRID 970038 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 230087101-Ethyl-5-aminoindolineYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-095a1822bc644a8e8b2af4bd3b51bb83
Source dataset
uspto-grants-2007_12
Patent number
US07309715B2

Reaction notes

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