Acetic Acid → HCID 19035986, compound

HRID 263903Notes

Reaction equation

HRID 263903 reaction equation
Cl[CH:2]1[C:14]2[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[C:17]([OH:20])(=[O:19])[CH3:18]>>[C:17]([O:20][CH:2]1[C:14]2[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2)(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 19035982HCID 19035982, compound

Product 1

HCID 19035986HCID 19035986, compoundYield 57.5%

Procedure

9-Chloro-9H-indeno[1,2-b]pyrazine-2,3(1H,4H)-dione (0.30 g, 1.28 mmol) was refluxed in 50 ml of acetic acid for 10 min. Activated carbon (100 mg) was added and the reaction mixture was filtered and evaporated in vacuo to about 3 ml, and 20 ml of water was added. The precipitate was filtered off and washed with water and dried to give 229 mg of the crude compound, which was recrystallized from acetic acid-water to yield 190 mg (57.5%) of the title compound. M.p.>300° C. 1H-NMR (DMSO-d6, δ): 2.13 (s, 3H), 6.36 (s, 1H), 7.15 (t, 1H), 7.29 (d, 1H) 7.35 (t, 1H), 7.5 (d, 1H), 12.0 (s, 1H), 12.4 (s, 1H).

Workup

  1. additionActivated carbon (100 mg) was added
  2. filtrationthe reaction mixture was filtered
  3. customevaporated in vacuo to about 3 ml, and 20 ml of water
  4. additionwas added
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customdried
  8. customto give 229 mg of the crude compound, which
  9. customwas recrystallized from acetic acid-water

Sources & evidence

ORD record
ord-ad6eb70e97de4e0687da9a0c5f56fb44
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Reaction notes

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