Hydrochloric Acid → HCID 69071243, compound

HRID 2374485Notes

Reaction equation

HRID 2374485 reaction equation
[CH2:1]([C:3]1([CH2:23][CH3:24])[C:11]2[C:6](=[CH:7][C:8]([N+:16]([O-:18])=[O:17])=[C:9]([NH:12]C(=O)C)[CH:10]=2)[N:5]([CH:19]([CH3:21])[CH3:20])[C:4]1=[O:22])[CH3:2].Cl>C(O)C>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[N+:16]([O-:18])=[O:17])[N:5]([CH:19]([CH3:20])[CH3:21])[C:4](=[O:22])[C:3]2([CH2:23][CH3:24])[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69068910HCID 69068910, compound

Product 1

HCID 69071243HCID 69071243, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3,3-diethyl-1-isopropyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (2.2 g, 6.60 mmol) was dissolved in ethanol (50 ml). After addition of hydrochloric acid (25%, 3.2 ml, 33.0 mmol) the mixture was heated under reflux for 3 h. Most of the solvent was evaporated and water was added. The mixture was weakly alkalized by addition of aqueous NaOH solution. The mixture was extracted with ethyl acetate, the combined organic phases were dried over magnesium sulfate and the solvent was evaporated to yield 1.9 g 5-amino-3,3-diethyl-1-isopropyl-6-nitro-1,3-dihydro-indol-2-one (6.52 mmol, 99%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customMost of the solvent was evaporated
  4. additionwater was added
  5. additionThe mixture was weakly alkalized by addition of aqueous NaOH solution
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialthe combined organic phases were dried over magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a5cd54a306514872a8599130a3577861
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

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