Sodium Hydroxide → 4,5-Dihydro-4,10-dioxoimidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid

HRID 1609Notes

Reaction equation

HRID 1609 reaction equation
[OH-:1].[Na+].[O:3]=[C:4]1[NH:9][C:8]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:16][C:7]=2[N:6]2[CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[N:19]=[C:5]12>O1CCOCC1>[O:3]=[C:4]1[NH:9][C:8]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:16](=[O:1])[C:7]=2[N:6]2[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=[C:5]12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19691063ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate

Product 1

HCID 196910474,5-Dihydro-4,10-dioxoimidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5 ml of 1N sodium hydroxide are added to a suspension of 0.2 g of ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in 15 ml of dioxane, and the reaction mixture is stirred vigorously while compressed air is bubbled for 15 hours. After addition of 10 ml of distilled water the mixture is acidified with concentrated hydrochloric acid. The precipitate form is filtered off, washed with water and dried to produce 0.13 g of 4,5-dihydro-4,10-dioxoimidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid in the form of a brown powder whose melting point is higher than 260° C. (1H spectrum in DMSO, T=300K, δ in ppm (200 MHz): between 7.35 and 7.65 (3H, m, CH arom. ), 7.75 (1H, d, J=7 Hz, CH arom.), 8.38 (1H, s, CH arom.), 12.5 (1H, s, NH)).

Workup

  1. customis bubbled for 15 hours
  2. additionAfter addition of 10 ml of distilled water the mixture
  3. filtrationThe precipitate form is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6c6c6d89b5d34913acc93848722ce98e
Source dataset
uspto-grants-1998_03
Patent number
US05726175

Reaction notes

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