Hydrochloric Acid → HCID 18975428, compound

HRID 2393406Notes

Reaction equation

HRID 2393406 reaction equation
[CH3:1][C:2]1([CH2:19][C:20]#N)[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.Cl.[OH-:23].[Na+].[OH2:25]>>[CH3:1][C:2]1([CH2:19][C:20]([OH:25])=[O:23])[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18975466HCID 18975466, compound

Product 1

HCID 18975428HCID 18975428, compound

Conditions

Temperature
20 °C

Procedure

The process is performed as in Example 53 but starting with 0.84 g of (10-methyl-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)-acetonitrile, 7.6 ml of concentrated hydrochloric acid and 1.5 ml of distilled water. The reaction mixture is cooled to a temperature in the region of 20° C., basified with 7 ml of concentrated sodium hydroxide and filtered. Distilled water (qs 50 ml) is added and the filtrate is acidified to pH 4 with acetic acid. The precipitate formed is filtered off, washed with distilled water and then with ethyl ether (2×15 ml), and dried at 60° C. under vacuum (1 mmHg; 0.13 kPa). 0.14 g of (10-methyl-4,5-dihydro-4-oxo-10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetic acid is obtained in the form of a beige-coloured solid (1H NMR spectrum: (200 MHz; (CD3)2SO-d6 ; δ in ppm): 1.62 (s, 3H: CH3); 3.22 (limiting AB, J=15.5 Hz, 1H: CH2COO); 7.35 (mt, 2H: H 7 and H 8); 7.60 and 8.28 (2 broad s, 1H each: H of the imidazole); 7.65 and 7.85 (2 broad d, J=7.5 Hz, 1H each: H 6 and H 8); from 11.80 to 12.80 (broad mult., 1H: NH 5)).

Workup

  1. filtrationfiltered
  2. additionDistilled water (qs 50 ml) is added
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washwashed with distilled water
  6. dry with materialwith ethyl ether (2×15 ml), and dried at 60° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-a16870225acc451ab0d54cb38dc3a8f6
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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