Hydrochloric Acid → HCID 53747692, compound

HRID 1870814Notes

Reaction equation

HRID 1870814 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]=[C:14]2[C:19](=[O:20])[NH:18][C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH2:28][C:29](OCC)=[O:30])[C:26]=4[CH2:27][C:16]=3[N:15]2[CH:34]=1)([O:3]CC)=[O:2].[ClH:35]>>[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]=[C:14]2[C:19](=[O:20])[NH:18][C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH2:28][C:29]([Cl:35])=[O:30])[C:26]=4[CH2:27][C:16]=3[N:15]2[CH:34]=1)([OH:3])=[O:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 18694064HCID 18694064, compound

Product 1

HCID 53747692HCID 53747692, compound

Procedure

A stirred solution of 1.3 g of ethyl 2-(2-carbethoxyphenyl)-4-oxo-4,5-dihydro-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-9-acetate in 45 ml of a 12 N aqueous hydrochloric acid solution is maintained at boiling temperature for 64 hours. After cooling, the insoluble matter is separated by filtration, washed 3 times with a total of 45 ml of distilled water and dried under reduced pressure (0.5 mm Hg; 0.07 kPa) at 45° C. 0.9 g of 2-(2-carboxyphenyl)-4-oxo-4,5-dihydro-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-9-acetic acid chloride is thus obtained in the form of a dark grey solid which decomposes without melting above 260° C. [1H NMR spectrum in DMSO-d6, T=300K, δ in ppm (250 MHz); 3.75 (2H, s, CH2), 4.05 (2H, s, CH2), 7.25 (1H, d, J=7 Hz, arom. CH), 7.40 (1H, t, J=7 Hz, arom. CH), between 7.50 and 8.10 (5H, m, 5 arom. CH), 8.45 (1H, s, imidazole CH), 13.00 (1H, broad s, NHCO)].

Workup

  1. customfor 64 hours
  2. temperatureAfter cooling
  3. customthe insoluble matter is separated by filtration
  4. washwashed 3 times with a total of 45 ml of distilled water
  5. customdried under reduced pressure (0.5 mm Hg; 0.07 kPa) at 45° C

Sources & evidence

ORD record
ord-28a167a1201f4ea6a412adcd8224f254
Source dataset
uspto-grants-2000_08
Patent number
US06100264

Reaction notes

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