Hydrochloric Acid → 1-Ethyl-5-nitro-indoline

HRID 1836281Notes

Reaction equation

HRID 1836281 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].Cl>>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)[CH3:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 36566Ethanone, 1-(2,3-dihydro-5-nitro-1H-indol-1-yl)-

Product 1

HCID 234991451-Ethyl-5-nitro-indolineYield 109.4%

Conditions

Temperature
50 °C

Procedure

1-Acetyl-5-nitro-indoline (1.00 g, 4.85 mmol) was added to borane-THF complex (1 M, 10 mL, 10 mmol). The mixture was heated at reflux for 4 h. With ice-water bath cooling, the mixture was slowly treated with 6 N HCl (4 mL). Then the mixture was heated at 50° C. for 1 h. The organic solvent was evaporated off and the resulting suspension was filtered to give an orange solid (1.02 g) which was washed with water: mp 97-98° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureWith ice-water bath cooling
  4. customThe organic solvent was evaporated off
  5. filtrationthe resulting suspension was filtered

Sources & evidence

ORD record
ord-1799484f93ee429bbbcc8e4c27e14ea9
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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