p-Fluoronitrobenzene → HCID 58998396, compound

HRID 1593042Notes

Reaction equation

HRID 1593042 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].F[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 218898267-FLUORO-6-METHOXYISOQUINOLIN-1(2H)-ONE

Product 1

HCID 58998396HCID 58998396, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 11.0 g of 7-Fluoro-6-methoxy-2H-isoquinolin-1-one (57 mmol) in DMF (108 mL) was added potassium carbonate (11.8 g), followed by 10.6 g of 1-fluoro-4-nitrobenzene (75 mmol). The reaction mixture was stirred at 120° C. for 6 hr then poured onto ice water. The slurry was extracted with ether to remove excess pFPhNO2. The precipitate was collected by filtration, washed with ether and dried in vacuo to give 12.1 g (68%) of the product asa yellow solid. RP-HPLC: 4.79 min; ES-MS (M+H)+=315.0; 1H-NMR (DMSO-d6) δ (ppm): 4.0 (3H, s), 6.76 (1,d), 7.48 (d, 1), 7.53 (d, 1), 7.83 (d,2), 7.92 (d, 1), 8.38 (d, 2).

Workup

  1. additionthen poured onto ice water
  2. extractionThe slurry was extracted with ether
  3. customto remove excess pFPhNO2
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-29e1611d24334519b3415b0fc6310c36
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

Loading…