Hydrochloric Acid → 3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

HRID 1014281Notes

Reaction equation

C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:16][CH3:17])=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=2)[C:6]([CH3:19])([CH3:18])[CH2:5]1)(=O)C.Cl.O1CCOCC1>CO>[CH3:18][C:6]1([CH3:19])[C:7]2[C:12](=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([O:16][CH3:17])[CH:8]=2)[NH:4][CH2:5]1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 1-acetyl-3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (2.55 g, 9.65 mmol) in methanol (75 mL) was treated with 4.0N HCl in dioxane (19.30 mL, 77 mmol) and maintained at 70° C. for 16 hours. The solution was concentrated under reduced pressure, solids were triturated with diethyl ether and the slurry was filtered to afford 3,3-dimethyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (2.340 g, 94% yield) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.68 (s, 1 H), 7.36 (s, 1 H), 3.89 (s, 3 H), 3.41 (s, 2 H), 1.33 (s, 6 H).

Workup

concentrationThe solution was concentrated under reduced pressure, solids
customwere triturated with diethyl ether
filtrationthe slurry was filtered

Sources & evidence

ORD record: ord-2f2b02ff998841d18107229f87c88bef
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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