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

HRID 507353

Reaction equation

HRID 507353 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-])=O)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(O)C.C1COCC1.[Pd]>[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:3])[CH3:2]

Participants

4

Reactant 1

HCID 36566Ethanone, 1-(2,3-dihydro-5-nitro-1H-indol-1-yl)-

Product 1

HCID 2925071-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-oneYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The solution of 1-acetyl-5-nitroindoline (1.0 g, 4.85 mmol) in ethanol-THF (100 mL: 30 mL) was hydrogenated over 5% Pd/C (600 mg) at atmosphere pressure for 2 h, filtered through Celite and concentrated in vacuo to give a white solid which was recrystallized from ethanol. White crystalline solid (580 mg, 68%) was obtained. Mp 185-186.5° C. (lit 184-185° C., [21]); 1H NMR (270 MHz, DMSO): δ 7.73 (1H, d, J=8.6 Hz, ArH), 6.45 (1H, s broad, w1/2=1.8 Hz, ArH), 6.33 (1H, dd, J=8.6, 1.8 Hz, ArH), 4.82 (2H, s, NH2), 3.97 (2H, t, J=8.4 Hz, CH2), 2.99 (2H, t, J=8.4 Hz, CH2), 2.07 (3H, s, CH3); APCI-MS 175 (M−H+).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. customto give a white solid which
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-faa1201d1fb64738a089096971443990
Source dataset
uspto-grants-2010_08
Patent number
US07786152B2

Linked notes

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