Nitric Acid → 3,3-Dimethyl-6-nitroindoline

HRID 470655Notes

Reaction equation

HRID 470655 reaction equation
OS(O)(=O)=O.Cl.[CH3:7][C:8]1([CH3:17])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH2:9]1.[N+:18]([O-])([OH:20])=[O:19].[NH4+].[OH-]>O>[CH3:7][C:8]1([CH3:17])[C:16]2[C:11](=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[CH:14][CH:15]=2)[NH:10][CH2:9]1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14923Ammonium Hydroxide2×HCID 674245941231953-20-0

Product 1

HCID 219594663,3-Dimethyl-6-nitroindoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-2.5 °C

Procedure

H2SO4 (1.42 kg) and 3,3-dimethylindoline HCl salt (Example 3, 200 g) were charged to a dry 5 L RB-flask under nitrogen at 20-25° C. The reaction mixture was cooled to −15 to 10° C. A solution of HNO3 (75.6 g) in water (18.89 g) was added drop-wise. The resulting reaction mixture was stirred for 1 h. The mixture was transferred into a mixture of 2.084 L of 30% NH4OH and 600 mL of water at 0-5° C. The pH was adjusted to 8-9 with NH4OH, and after the addition of 800 mL of IPAC, phases were separated. The aqueous phase was extracted with IPAC (400 mL). The combined organic phase was washed with saturated brine (400 mL) to give a solution of 3,3-dimethyl-6-nitroindoline. (190.5 g, 91%, 94 A %).

Workup

  1. customThe resulting reaction mixture
  2. additionafter the addition of 800 mL of IPAC, phases
  3. customwere separated
  4. extractionThe aqueous phase was extracted with IPAC (400 mL)
  5. washThe combined organic phase was washed with saturated brine (400 mL)

Sources & evidence

ORD record
ord-a455e557e766490faa09973d323170c2
Source dataset
uspto-grants-2014_01
Patent number
US08629289B2

Reaction notes

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