Hydrochloric Acid → HCID 54574915, compound

HRID 581704Notes

Reaction equation

HRID 581704 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([CH2:18][C:19]([O:21]CC)=[O:20])([CH3:17])[C:13]2[C:3]=1[CH:4]=[C:5]1[NH:10][C:9](=[O:11])[C:8](=[O:12])[NH:7][C:6]1=2.O1CCOCC1.Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([CH2:18][C:19]([OH:21])=[O:20])([CH3:17])[C:13]2[C:3]=1[CH:4]=[C:5]1[NH:10][C:9](=[O:11])[C:8](=[O:12])[NH:7][C:6]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86754196HCID 86754196, compound

Product 1

HCID 54574915HCID 54574915, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.27 g of ethyl (8-chloro-5-methyl-2,3-dioxo-1,4-dihydro-5H-indeno [1,2-b]pyrazin-5-yl)acetate, 120 ml of dioxane and 25 ml of 8N aqueous hydrochloric acid solution is heated to a temperature in the region of 80° C. for 4 hours. The reaction mixture is then evaporated under reduced pressure, and the evaporation residue is triturated in 35 ml of an ethanol/water (85:15 by volume) mixture, filtered and washed with distilled water (2 times 10 ml). The product obtained is taken up in 68 ml of 0.1N aqueous sodium hydroxide solution. The insoluble matter is separated by filtration, and the filtrate is neutralized by adding 6.8 ml of 1N aqueous hydrochloric acid solution. The solid obtained is separated by filtration, washed with distilled water (2 times 5 ml) and dried in the air. 0.41 g of (8-chloro-5-methyl-2,3-dioxo-1,4-dihydro-5H-indeno[1,2-b]pyrazin-5-yl) acetic acid is thereby obtained in the form of an ochre-coloured solid melting above 300° C. (1H NMR spectrum [200 MHz, (CD3)2SO-d6, δ in ppm]: 1.39 (3H, s, CH3); 2.93 (2H, m, --CH2 --CO); 7.19 (lH, dd, J=8 and 2 Hz, arom H); 7.48 (1H, d, J=8 Hz, arom H); 7.56 (1H, d, 2=2 Hz, arom H); 12.18 (1H, s, --NH--); 12.24, s, --NH); Analysis, % calculated C: 54.83; H: 3.61; Cl: 11.56; N: 9.13; 0: 20.87; % found C: 55.2; H: 3.4; Cl: 11.2; N: 9.0; O: 18.6).

Workup

  1. customThe reaction mixture is then evaporated under reduced pressure
  2. customthe evaporation residue is triturated in 35 ml of an ethanol/water (85:15 by volume) mixture
  3. filtrationfiltered
  4. washwashed with distilled water (2 times 10 ml)
  5. customThe product obtained
  6. customThe insoluble matter is separated by filtration
  7. additionby adding 6.8 ml of 1N aqueous hydrochloric acid solution
  8. customThe solid obtained
  9. customis separated by filtration
  10. washwashed with distilled water (2 times 5 ml)
  11. customdried in the air

Sources & evidence

ORD record
ord-3136d046ff6047b39e4542c88f693cd6
Source dataset
uspto-grants-1999_07
Patent number
US05922716

Reaction notes

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