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

HRID 238508Notes

Reaction equation

HRID 238508 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-fb5c69e5fa60499cb5685b37998bf572
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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