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

HRID 887562Notes

Reaction equation

HRID 887562 reaction equation
[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4](C(=O)C)[CH2:3]1.Cl>CCO>[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 161274181-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

Product 1

HCID 219594663,3-Dimethyl-6-nitroindoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1-(3,3-Dimethyl-6-nitro-2,3-dihydro-indol-1-yl)ethanone (1.8 g) was dissolved in EtOH (50 mL), 12N HCl (50 mL) was added and the resulting mixture was heated at 70° C. overnight. After the mixture was concentrated in vacuo, it was partitioned between saturated NaHCO3 solution and EtOAc, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford a yellow solid. MS: 193 (M+1). Calc'd. for C10H12N2O2—192.21.

Workup

  1. concentrationAfter the mixture was concentrated in vacuo, it
  2. customwas partitioned between saturated NaHCO3 solution and EtOAc
  3. dry with materialthe resulting organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow solid

Sources & evidence

ORD record
ord-e41e6183b7a84ed0ae4f9305f36cc686
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

Loading…