5-Nitro-6-bromo-1h,3h-benzo[de]isochromene → 5-Nitro-1,3-dihydrobenzo[de]isochromene-6-carbonitrile

HRID 217285Notes

Reaction equation

HRID 217285 reaction equation
[N+:1]([C:4]1[C:5](Br)=[C:6]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:7]2=[C:8]([CH:16]=1)[CH2:9][O:10][CH2:11]3)([O-:3])=[O:2].[Cu][C:19]#[N:20]>CN(C=O)C>[N+:1]([C:4]1[C:5]([C:19]#[N:20])=[C:6]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:7]2=[C:8]([CH:16]=1)[CH2:9][O:10][CH2:11]3)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 578987455-Nitro-6-bromo-1h,3h-benzo[de]isochromeneHCID 178418546HCID 178418546, compound

Product 1

HCID 578986665-Nitro-1,3-dihydrobenzo[de]isochromene-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

5-Nitro-6-bromo-1H,3H-benzo[de]isochromene (23.0 g, 78.2 mmol) was dissolved in anhydrous DMF (500 mL). Then, copper (I) cyanide (10.5 g, 117 mmol) was added to the mixture at room temperature. The mixture was stirred at the internal temperature of 140° C. for 3 hours, and then cooled to 70° C. The resulting insoluble material was separated by filtration. The filtrate was poured into water (1500 mL), and stirred at room temperature for 2 hours. The resulting precipitate was collected by filtration, washed with acetonitrile, and air-dried. The title compound was obtained as yellow solid (15.9 g, 85%).

Workup

  1. temperaturecooled to 70° C
  2. customThe resulting insoluble material was separated by filtration
  3. additionThe filtrate was poured into water (1500 mL)
  4. stirringstirred at room temperature for 2 hours
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with acetonitrile
  7. customair-dried

Sources & evidence

ORD record
ord-216c678032994032a92faa91f22a2592
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

Loading…