1-(5-Methoxy-6-nitroindolin-1-yl)ethanone → 1-(6-Amino-5-methoxyindolin-1-yl)ethanone

HRID 1014271Notes

Reaction equation

HRID 1014271 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:16][CH3:17])=[C:10]([N+:13]([O-])=O)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>CCO.[Pd]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:16][CH3:17])=[C:10]([NH2:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 594416551-(5-Methoxy-6-nitroindolin-1-yl)ethanone

Product 1

HCID 594418241-(6-Amino-5-methoxyindolin-1-yl)ethanoneYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-acetyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole Intermediate B98 (0.56 g, 2.37 mmol) and 10% Pd on carbon (500 mg) in EtOH (100 mL) was stirred overnight under 1 atm of H2 gas, then was filtered through a pad of Celite. The filtrate was concentrated to dryness. The residue was dissolved in CH2Cl2 and purified by silica gel chromatography using 30-60% EtOAc/CH2Cl2to obtain 1-acetyl-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine as a white solid (327 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.09 s, 3H), 2.98 (t, J=8.33 Hz 2H), 3.70 (s, 3H), 3.99 (t, J=8.33 Hz, 2H), 4.62 (s, 2H), 6.69 (s, 1H), 7.52 (s, 1H); ESIMS (M+H)+=207.

Workup

  1. filtrationwas filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated to dryness
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-81a2e56f9b5e44a8ac0bce614bc72fa8
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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