4-Methyl-5-nitro-3-(3-hydroxypropyl)indole → HCID 19962055, compound

HRID 441097Notes

Reaction equation

HRID 441097 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:5][NH:6]2>C(O)C.[Pd]>[CH3:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:5][NH:6]2

Participants

4

Reactant 1

HCID 199620414-Methyl-5-nitro-3-(3-hydroxypropyl)indole

Product 1

HCID 19962055HCID 19962055, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-methyl-5-nitro-3-(3-hydroxypropyl)indole (0.365 g, 1.56 mmol) in 20 mL of absolute ethanol was added 10% palladium-on-charcoal (0.150 g) and the mixture was hydrogenated on a Parr shaker at 50 psi for 0.5 h. The mixture was then filtered through a plug of Celite, the catalyst was washed with additional ethanol and the filtrate was evaporated to give the title compound (0.280 g, 88%) as a solid. An analytical sample was crystallized from ethyl acetate to give cream-coloured needles, mp 141°-142° C.: IR (KBr) 3388, 3180, 1618 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ 10.20 (br s, 1H), 6.87 (d, J=8.8 Hz, 1H), 6.83 (s, 1H), 6.50 (d, J=8.3 Hz, 1H), 4.43 (t, J=5.2 Hz, 1H), 4.12 (s, 2H), 3.47 (dt, J=6.4, 5.3 Hz, 2H), 2.79 (t, J=7.7 Hz, 2H), 2.31 (s, 3H), 1.73 (m, 2H). Anal. Calcd for C12H16N2O: C, 70.55; H, 7.90; N, 13.72. Found: C, 70.41; H, 7.89; N, 13.55.

Workup

  1. filtrationThe mixture was then filtered through a plug of Celite
  2. washthe catalyst was washed with additional ethanol
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2171d34d8523410ebb3af56ff4ee27bd
Source dataset
uspto-grants-1996_05
Patent number
US05521188

Reaction notes

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