Hydrochloric Acid → 5-methoxy-6-nitro-2,3-dihydro-1H-indole

HRID 1014251Notes

Reaction equation

HRID 1014251 reaction equation
Cl.C([N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[CH2:7][CH2:6]1)(=O)C>CO>[CH3:18][O:17][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15])[NH:5][CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594416551-(5-Methoxy-6-nitroindolin-1-yl)ethanone

Product 1

HCID 594416565-methoxy-6-nitro-2,3-dihydro-1H-indoleYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of conc. HCl (20 mL) in methanol (40 mL) was added 1-acetyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (7.8 g, 33 mmol) and the resulting mixture was refluxed for 4 hours. After cooling, the solvent was removed in vacuo, the residue was neutralized with saturated aqueous sodium hydrogencarbonate solution, and a brown precipitate formed. The precipitate was filtered via Buchner funnel, washed with water, and dried under reduced pressure to give 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole as a brown solid (6.1 g, 94% yield). 1H-NMR (DMSO, 300 MHz) δ 7.11 (s, 1H), 6.87 (s, 1H), 5.59 (brs, 1H), 3.78 (s, 3H), 3.43 (t, 2H), 2.97 (t, 2H).

Workup

  1. temperaturethe resulting mixture was refluxed for 4 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. customa brown precipitate formed
  5. filtrationThe precipitate was filtered via Buchner funnel
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-0a34d70c3c70491580eddf989da8ed4b
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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