Ammonium Acetate → HCID 18790698, compound

HRID 1107037Notes

Reaction equation

[C:1]1(=[O:32])[N:5]([CH2:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[C:12](=O)[CH:11]([N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[C:22](OCC)=[O:23])[CH2:10]3)[C:4](=[O:27])[C:3]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:2]12.C([O-])(=O)C.[NH4+:37]>C(O)(=O)C>[C:4]1(=[O:27])[N:5]([CH2:6][C:7]2[CH:15]=[CH:14][C:13]3[C:12]4[NH:37][C:22](=[O:23])[C:18]5[N:17]([CH:21]=[CH:20][N:19]=5)[C:11]=4[CH2:10][C:9]=3[CH:8]=2)[C:1](=[O:32])[C:2]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:3]12

Participants

Conditions

Temperature: 20 °C

Procedure

8-Phthalimidomethyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one can be obtained in the following way: a mixture of 17 g of ethyl 1-(5-phthalimidomethyl-1oxoindan-2yl)imidazole-2-carboxylate and 153 g of ammonium acetate in 355 ml of glacial acetic acid is heated at reflux for 16 hours. The reaction mixture is cooled to a temperature in the region of 20° C. The precipitate is filtered on sintered glass, rinsed with distilled water to neutral pH and then washed with acetone. After drying under vacuum (1 mbar) at 80° C., 10 g of 8-phthalimidomethyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one are obtained in the form of a brown solid (1H NMR spectrum in d6-DMSO, T=300 K, δ in ppm: 4.00 (2H, s, CH2), 4.83 (2H, s, NCH2), 7.47 (1H, d, J=7 Hz, arom. CH), 7.55 (2H, d, J=7 Hz, arom. CH), 7.80 (1H, d,J=7 Hz, arom. CH), between 7.85 and 8.00 (4H, m, phthal. H), 12.30 (1H, broad s, NH)).

Workup

temperatureis heated
temperatureat reflux for 16 hours
filtrationThe precipitate is filtered on sintered glass
washrinsed with distilled water to neutral pH
washwashed with acetone
customAfter drying under vacuum (1 mbar) at 80° C.

Sources & evidence

ORD record: ord-8fb4361198ed4761aee49844aeb64189
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057454

Reaction notes

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