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

HRID 2247267Notes

Reaction equation

HRID 2247267 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, Step C) 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-f1ad3e4663e64cb4af4957b171347bed
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

Loading…