Hydrochloric Acid → HCID 67316756, compound

HRID 1014395Notes

Reaction equation

HRID 1014395 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 59441628HCID 59441628, compound

Product 1

HCID 67316756HCID 67316756, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of (2R)-1-acetyl-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (5.78 g, 23.10 mmol) in MeOH (50 mL) and a 4N HCl solution in dioxane (57.7 mL, 231 mmol) was heated at 70° C. for 8 h. The resulting mixture was allowed to cool to rt and concentrated to afford (2R)-2-methyl-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole hydrogen chloride as a brown sticky solid (5.47 g, 97%). 1FI NMR (400 MHz, DMSO-d6) δ ppm 1.38 (d, J=6.59 Hz, 3H), 2.82 (dd, J=16.85, 7.69 Hz, 1H), 3.32 (dd, J=16.85, 8.06 Hz, 1H), 3.90 (s, 3H), 4.09-4.26 (m, 1H), 7.39 (s, 1H), 7.60 (s, 1H); ESIMS (M+H)+=209.00.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-2af548b793d0440cbc215a80d053ab5b
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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