Hydrochloric Acid → HCID 18694022, compound

HRID 1603712Notes

Reaction equation

HRID 1603712 reaction equation
[C:1]([CH2:4][C:5]1[C:6]2[CH2:7][C:8]3[N:13]4[CH:14]=[C:15](/[CH:17]=[CH:18]/[C:19]([O:21]CC)=[O:20])[N:16]=[C:12]4[C:11](=[O:24])[NH:10][C:9]=3[C:25]=2[CH:26]=[CH:27][CH:28]=1)([OH:3])=[O:2].Cl>C(O)(=O)C>[C:1]([CH2:4][C:5]1[C:6]2[CH2:7][C:8]3[N:13]4[CH:14]=[C:15](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[N:16]=[C:12]4[C:11](=[O:24])[NH:10][C:9]=3[C:25]=2[CH:26]=[CH:27][CH:28]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86754834HCID 86754834, compound

Product 1

HCID 18694022HCID 18694022, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.45 g of ethyl (E)-3-(9-carboxymethyl-4-oxo-5,10-dihydroimidazo[1,2-a]indeno[1,2-e]pyrazin-2-yl)acrylate, 19 ml of concentrated hydrochloric acid and 78 ml of acetic acid is heated at reflux for 48 hours. The reaction mixture is filtered and the solid is washed with 2×20 ml of distilled water and then with 2×10 ml of acetone and finally dried under vacuum (1 mm Hg; 0.13 kPa) at about 60° C. 0.94 g of (E)-3-(9-carboxymethyl-4-oxo-5,10-dihydroimidazo[1,2-a]indeno[1,2-e]pyrazin-2-yl)acrylic acid is obtained in the form of a beige solid melting above 260° C. [Analysis: C18H13N3O5, 0.89 HCl, 0.91 H2O, % calculated C: 61.54, H: 3.73, N: 11.96, O: 22.77, % found C: 61.8, H: 3.4, N: 11.9].

Workup

  1. temperatureis heated
  2. temperatureat reflux for 48 hours
  3. filtrationThe reaction mixture is filtered
  4. washthe solid is washed with 2×20 ml of distilled water
  5. dry with materialwith 2×10 ml of acetone and finally dried under vacuum (1 mm Hg; 0.13 kPa) at about 60° C

Sources & evidence

ORD record
ord-d18b99a4bbee4760af1d4916d7e56276
Source dataset
uspto-grants-1999_11
Patent number
US05990108

Reaction notes

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