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

HRID 2109623Notes

Reaction equation

HRID 2109623 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 (Step C, 1.8 g) was dissolved in 50 mL EtOH, 50 mL 12N HCl was added and the resulting mixture was heated at 70° C. overnight. After the mixture was concentrated in vacuo, it was extracted 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 C10H12N2O2−192.2.

Workup

  1. concentrationAfter the mixture was concentrated in vacuo, it
  2. extractionwas extracted 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-a8c3599e248b4a9a9f9e50c56dc0acb0
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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