Nitric Acid → HCID 20094336, compound

HRID 273843Notes

Reaction equation

HRID 273843 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][CH:14]([Br:16])[CH3:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N+:17]([O-])([OH:19])=[O:18]>C(O)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][CH:14]([Br:16])[CH3:15])=[CH:10][C:11]=2[N+:17]([O-:19])=[O:18])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 200943701-[5-(2-Bromopropyl)-2,3-dihydro-1H-indol-1-yl]ethanone

Product 1

HCID 20094336HCID 20094336, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-acetyl-5-(2-bromopropyl)indoline (153 g) in acetic acid (240 ml) was added fuming nitric acid (120 ml) with stirring under ice cooling over a period of 1 hour, and the mixture was stirred at room temperature for 30 minutes. After the reaction mixture was poured into ice water slowly, the precipitates were collected by filtration, and dissolved in benzene (1.5 l). The benzene solution was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate-isopropyl ether to give 155 g of 1-acetyl-5-(2-bromopropyl)-7-nitroindoline melting at 119°-120° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. filtrationthe precipitates were collected by filtration
  3. dissolutiondissolved in benzene (1.5 l)
  4. washThe benzene solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-eac9aa3827ec4723b1d6eec944f571c8
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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