2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 23369702, compound

HRID 1900727Notes

Reaction equation

HRID 1900727 reaction equation
[C:1]([NH:4][CH2:5][CH:6]1[O:20][C:9]2=[C:10]3[C:15](=[C:16]([CH3:18])[CH:17]=[C:8]2[CH2:7]1)[NH:14][C:13](=[O:19])[CH:12]=[CH:11]3)(=[O:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(O)(=O)C>[C:1]([NH:4][CH2:5][C:6]1[O:20][C:9]2=[C:10]3[C:15](=[C:16]([CH3:18])[CH:17]=[C:8]2[CH:7]=1)[NH:14][C:13](=[O:19])[CH:12]=[CH:11]3)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 23369610HCID 23369610, compound

Product 1

HCID 23369702HCID 23369702, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

2-(N-Acetylaminomethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (750 mg) was suspended in acetic acid (15 ml), to which 2,3-dichloro-5,6-dicyano -1,4-benzoquinone (782 mg) was added. The mixture was stirred at 60° C. for 1 hour. The solvent was distilled off under reduced pressure. To the residue, aqueous 1N NaOH solution (50 ml) was added. Precipitated crystals were collected. As a result, 553 mg of 2-(N-acetylaminomethyl) -6,7-dihydro-5-methylfuro[2,3-f]quinoline-7-one (74.3%) was obtained.

Workup

  1. additionwas added
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionTo the residue, aqueous 1N NaOH solution (50 ml) was added
  4. customPrecipitated crystals
  5. customwere collected

Sources & evidence

ORD record
ord-4cc58c31f44240fba2bbbc2dc11befa9
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…