Acetic Anhydride → HCID 56988602, compound

HRID 2393371Notes

Reaction equation

HRID 2393371 reaction equation
[C:1]([CH:4]([CH:6]1[C:18]2[N:17]3[CH:19]=[CH:20][N:21]=[C:16]3[C:15](=[O:22])[NH:14][C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2)O)([OH:3])=[O:2].C(OC(=O)C)(=O)C>[Cl-].[Zn+2].[Cl-].O>[C:1]([CH:4]=[C:6]1[C:18]2[N:17]3[CH:19]=[CH:20][N:21]=[C:16]3[C:15](=[O:22])[NH:14][C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 18975447HCID 18975447, compound

Product 1

HCID 56988602HCID 56988602, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

2.4 g of 10-(1-carboxy-1-hydroxymethyl)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 20 ml of acetic anhydride and 20 mg of zinc chloride are heated to reflux for 4 hours, under cover of argon. The reaction mixture is treated with 25 ml of water and the precipitate formed is filtered off, washed with 25 ml of water and then with 2×25 ml of acetone and dried at 80° C. under vacuum (1 mmHg; 0.13 kPa) to give 0.52 g of 10-(carboxymethylene)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one in the form of an orange-yellow solid, which product is converted into the sodium salt of formula C15H8N3O3Na (Analysis, % calculated C: 59.81, H: 2.68, N: 13.95, O: 15.93, Na : 7.63, % found C 59.5, H: 2.1, N: 13.6).

Workup

  1. temperatureto reflux for 4 hours, under cover of argon
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with 25 ml of water
  5. dry with materialwith 2×25 ml of acetone and dried at 80° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-dc6add02c2ec4aeebb6d5e4887ff4212
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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