Acetic Acid → HCID 10726309, compound

HRID 1490106Notes

Reaction equation

HRID 1490106 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(=O)C.[N:17]#[C:18]Br.[OH-].[Na+]>C(O)C.O>[C:18]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH2:8][CH2:9]1)#[N:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10476Cyanogen BromideHCID 14798Sodium HydroxideHCID 297576-Nitroindoline

Product 1

HCID 10726309HCID 10726309, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

To a cooled (4° C.) and stirred solution of 6-nitroindoline (3.04 g) in a mixture of glacial acetic acid (22 ml), water (11 ml) and absolute ethanol (23 ml) was added solid cyanogen bromide (2.93 g) followed by 1N aqueous sodium hydroxide solution (25 ml) over 3 minutes. The mixture was then allowed to warm to room temperature, stirred for a further 21 hours and the solid formed was collected by filtration, washed with water and dried over phosphorous pentoxide to give the title compound (2.94 g) as a solid; δH (250 MHz, DMSO-d6) 7.90 (1H, dd, J=8.1 and 2.2 Hz), 7.55-7.50 (2H, m), 4.23 (2H, t, J=8.4 Hz), 3.30 (2H, t, J=8.4 Hz); m/z (CI) 189 (M-).

Workup

  1. temperatureto warm to room temperature
  2. customthe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. dry with materialdried over phosphorous pentoxide

Sources & evidence

ORD record
ord-362b14dbaff64ac2b5427ff730a1e9db
Source dataset
uspto-grants-1997_10
Patent number
US05681833

Reaction notes

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