Hydrochloric Acid → HCID 19827795, compound

HRID 1709221Notes

Reaction equation

HRID 1709221 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[NH2:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[CH2:31]([OH:33])[CH3:32].C(OCC)(=[O:36])C>[Pd].O>[C:17]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[C:9]3[C:10](=[CH:11][C:12]([F:15])=[CH:13][CH:14]=3)[NH:16][C:31](=[O:33])[C:32]2=[O:36])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 19827831HCID 19827831, compound

Product 1

HCID 19827795HCID 19827795, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 1.6 g (5,0 mmol) N-diphenylmethyl-2-amino-4fluoroaniline in 100 ml ethyl acetate was hydrogenated at atm. pressure by using 5% Pd/C (100 mg) as a catalyst. The reaction mixture was filtered and 4.2 ml (30 mmol) dry triethylamine was added. 3.4 ml (30 mmol) ethyl oxalylchloride was added dropwise, and the reaction mixture was stirred for 1 h. The reaction mixture was filtered and evaporated in vacuo to give an oil. A mixture of the oil, 40 ml 1N hydrochloric acid and 60 ml ethanol was stirred at 80° C. for 4 h. After cooling to 25° C. 50 ml H2O was added, and the precipitate was filtered off. The crude product was dissolved in 20 ml ethanol, filtered and evaporated in vacuo to give an oil. The oil was stirred with 30 ml water for 1 h. The product was filtered off and dried to give 0.4 g (23%) 1-diphenylmethyl-6-fluoroquinoxaline-2,3(1H,4H)-dione. M.p. 143.8° C., 1H-NMR (CDCl3): 8.5-6.5 (3H, m), 7.2 (10H, s) 3.8 (1H, m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. filtrationThe reaction mixture was filtered
  3. customevaporated in vacuo
  4. customto give an oil
  5. stirringwas stirred at 80° C. for 4 h
  6. filtrationthe precipitate was filtered off
  7. dissolutionThe crude product was dissolved in 20 ml ethanol
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give an oil
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-830e4b639f0547fba20040522dc6bee1
Source dataset
uspto-grants-1990_08
Patent number
US04948794

Reaction notes

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