HCID 86754194, compound → HCID 86754192, compound

HRID 581702Notes

Reaction equation

HRID 581702 reaction equation
C([NH:4][CH:5]1[C:19]2[C:9]([CH:10]=[C:11]3[NH:16][C:15](=[O:17])[C:14](=[O:18])[NH:13][C:12]3=2)=[C:8]([Cl:20])[CH:7]=[CH:6]1)(=O)C>Cl>[ClH:20].[NH2:4][CH:5]1[C:19]2[C:9]([CH:10]=[C:11]3[NH:16][C:15](=[O:17])[C:14](=[O:18])[NH:13][C:12]3=2)=[C:8]([Cl:20])[CH:7]=[CH:6]1

Participants

3

Reactant 1

HCID 86754194HCID 86754194, compound

Product 1

HCID 86754192HCID 86754192, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
20 °C

Procedure

0.39 g of 5-acetamido-8-chloro-1,4-dihydro-5H-indeno[1,2-b]pyrazine-2,3-dione suspended in 5 ml of 6N hydrochloric acid is brought to reflux for 5 hours. After cooling to a temperature in the region of 20° C., the insoluble matter is filtered off, washed with water and then with methanol and taken up in 10 ml of a mixture of hot water and methanol (50:50 by volume). After a few minutes of stirring, the insoluble matter is filtered off and dried under a partial vacuum (1 mm Hg; 0.13 kPa) to yield 0.1 g of 5-amino-8-chloro-1,4-dihydro-5H-indeno [1,2-b]pyrazine-2,3-dione hydrochloride in the form of a grey solid, the melting point of which is above 260° C. (1H NMR spectrum [250 MHz, (CD3)2SO-d6, δ in ppm): 5.15 (s, 1H: CH 9); 7.39 (dd, J=8 and 2 Hz, 1H: H 7); 7.71 (d, J=2 Hz, 1H: H 5); 7.75 (d, J=8 Hz), 1H: H 8); from 8.70 to 9.20 (spread unres. comp., 3H: NH3+Cl-); from 12.00 to 12.70 (spread unres. comp., 2H: NHCOCONH).

Workup

  1. temperatureto reflux for 5 hours
  2. filtrationthe insoluble matter is filtered off
  3. washwashed with water
  4. filtrationthe insoluble matter is filtered off
  5. customdried under a partial vacuum (1 mm Hg; 0.13 kPa)

Sources & evidence

ORD record
ord-0412bf5203a8495f85dfe863e22857e5
Source dataset
uspto-grants-1999_07
Patent number
US05922716

Reaction notes

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