Potassium Fluoride → HCID 639599, compound

HRID 411302Notes

Reaction equation

HRID 411302 reaction equation
[F-].[K+].[CH3:3][O:4][C:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([C:17]=2[C:19]#[C:20][Si](C)(C)C)=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([O:25][CH3:26])=[CH:7][CH:6]=1>CO>[CH3:3][O:4][C:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([C:17]=2[C:19]#[CH:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([O:25][CH3:26])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 639597HCID 639597, compound

Product 1

HCID 639599HCID 639599, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium fluoride (0.5 g, 9.0 mmol) was added to a solution of 1,4-dimethoxy-9-trimethylsilylethynylacridine (prepared as described in Preparation 2 above) (1 g, 3.0 mmol) in methanol (30 ml) and the mixture was stirred at reflux for 30 min. The solvent was evaporated and the residue was dissolved in CH2Cl2. The organic solution was washed with H2O, dried and evaporated to give the title compound (764 mg, 97%) as a brown solid; m.p. 155-157° C. (Et2O). IR (KBr): ν/cm−1=2100 (w, C≡C), 1625 (m, Ar), 1460 (m, Ar); 1H NMR (200 MHz, CDCl3): δH/ppm=3.98 (s, 3H, OCH3), 4.10 (s, 3H, OCH3), 4.20 (s, 1H, ≡CH), 6.75 (d, J=8.4 Hz, 1H, H-2), 6.92 (d, J=8.4 Hz, 1H, H-3), 7.62 (dd, J=8.4 and 7.4 Hz, 1H, H-7), 7.78 (dd, J=8.6 and 7.4 Hz, 1H, H-6), 8.36 (d, J=8.6 Hz, 1H, H-5), 8.66 (d, J=8.4 Hz, 1H, H-8); 13C NMR (75.4 MHz, CDCl3): δC/ppm=56.0 (q, OCH3), 56.1 (q, OCH3), 85.6 (s, ≡C), 92.7 (d, ≡C), 104.1 (d, C-2), 105.8 (d, C-3), 121.0 (s, C-9a), 124.2 (s, C-9), 126.2 (d, C-6), 127.1 (d, C-7), 127.8 (s, C-8a), 130.0 (d, C-8), 130.4 (d, C-5), 141.3 (s, C-4a), 147.5 (s, C-1), 149.3 (s, C-10a), 149.5 (s, C-4); MS (EI); m/z (%)=264 [M+1] (7), 263 [M+] (35), 248 (100); HRMS: calcd. for C17H13NO2 263.0946; found 263.0940.

Workup

  1. temperatureat reflux for 30 min
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washThe organic solution was washed with H2O
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-39589929363e446da8fb4552621c0763
Source dataset
uspto-grants-2003_05
Patent number
US06559161B1

Reaction notes

Loading…