Nitrogen → 1-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-methyl-1-oxo-2-propanol

HRID 1014330Notes

Reaction equation

HRID 1014330 reaction equation
[CH3:1][C:2]([OH:20])([CH3:19])[C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].N#N>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][N:5]2[C:3](=[O:4])[C:2]([CH3:1])([OH:20])[CH3:19])=[CH:9][C:10]=1[O:17][CH3:18]

Participants

6

Reactant 2

HCID 947NitrogenHCID 594421262-methyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanol

Product 1

HCID 594417381-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-methyl-1-oxo-2-propanolYield 93.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanol (840 mg, 3.00 mmol) in ethyl acetate (100 mL) and Ethanol (50 mL) was degassed with N2 and to this was added 10% Pd/C (31.9 mg, 0.300 mmol). The reaction was maintained at 50 psi H2(g) overnight at rt on the Fisher-Porter apparatus. The catalyst was removed by vacuum filtration, rinsed with ethyl acetate (200 mL), and the filtrate was concentrated under reduced pressure to provide 1-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-2-methyl-1-oxo-2-propanol (0.7 g, 93%). ESIMS (M+H)+=251. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36 (s, 6H) 2.91 (t, J=8.03 Hz, 2 H) 3.71 (s, 3 H) 4.31 (t, J=8.03 Hz, 2 H) 4.57 (s, 2 H) 5.36 (s, 1 H), 6.70 (s, 1 H) 7.57 (s, 1 H).

Workup

  1. customThe catalyst was removed by vacuum filtration
  2. washrinsed with ethyl acetate (200 mL)
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f8700c0073124001afc3716ff0a88397
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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