Hydrochloric Acid → HCID 67316649, compound

HRID 1014399Notes

Reaction equation

HRID 1014399 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)[CH2:6][C@@H:5]1[CH3:18])(=O)C.[ClH:19].O1CCOCC1>CO>[ClH:19].[CH3:18][C@H:5]1[CH2:6][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]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59441786HCID 59441786, compound

Product 1

HCID 67316649HCID 67316649, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of (2S)-1-acetyl-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (5.7 g, 22.78 mmol) in MeOH (50 mL) and a 4N HCl solution in dioxane (56.9 mL, 228 mmol) was heated at 70° C. for 10 h. The resulting mixture was allowed to cool to rt and concentrated to afford (2S)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrogen chloride as a beige solid (5.55 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.39 (d, J=6.41 Hz, 3H), 2.84 (dd, J=16.94, 7.60 Hz, 1H), 3.34 (dd, J=16.85, 8.06 Hz, 1H), 3.90 (s, 3H), 4.12-4.27 (m, 1H), 7.41 (s, 1H), 7.66 (s, 1H); ESIMS (M+H)+=209.00.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-5ee1d65e91fc457ab1fea5c7bcc7c772
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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