Ammonium Acetate → HCID 18790711, compound

HRID 1075524Notes

Reaction equation

HRID 1075524 reaction equation
[CH2:1]([NH:3][C:4]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=O)[CH:11]([N:17]1[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=[C:18]1[C:27]([O:29]CC)=O)[CH2:10]2)=[O:5])[CH3:2].C([O-])(=O)C.[NH4+:36]>C(O)(=O)C>[CH2:1]([NH:3][C:4]([CH2:6][C:7]1[CH:15]=[CH:14][C:13]2[C:12]3[NH:36][C:27](=[O:29])[C:18]4[N:17]([CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=4)[C:11]=3[CH2:10][C:9]=2[CH:8]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 18790641HCID 18790641, compound

Product 1

HCID 18790711HCID 18790711, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.9 g of diethyl 1-[5-(N-ethylaminocarbonylmethyl)-1-oxoindan-2-yl]imidazole-2,4-dicarboxylate, 33.4 g of ammonium acetate and 200 ml of acetic acid is heated at reflux for 3 hours. The reaction mixture is evaporated on a rotary evaporator, 250 ml of distilled water are added to the evaporation residue and the residue is filtered. The solid obtained is washed with distilled water a number of times and dried in an oven. 2.2 g of ethyl 8-(N-ethylaminocarbonylmethyl)-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylate are obtained in the form of a light-brown solid melting above 300° C. (1H NMR spectrum in d6-DMSO, T=300K, δ in ppm (300 MHz): 1.05 (3H, t, J=6 Hz, CH3), 1.40 (3H, t, J=6 Hz, CH3), 3.12 (2H, m, NCH2), 3.48 (2H, s, CH2CO), 4.05 (2H, s, CH2), 4.40 (2H, q, J=6 Hz, CH2O), 7.32 (1H, d, J=8 Hz, arom. CH), 7.42 (1H, s, arom. CH), 7.83 (1H, d, J=8 Hz, arom. CH), 8.10 (1H, t, J=5 Hz, NH), 8.60 (1H, s, imidazole H)).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. customThe reaction mixture is evaporated on a rotary evaporator, 250 ml of distilled water
  4. additionare added to the evaporation residue
  5. filtrationthe residue is filtered
  6. customThe solid obtained
  7. washis washed with distilled water a number of times
  8. customdried in an oven

Sources & evidence

ORD record
ord-83d0df43054d4b60a1ef90943e417c64
Source dataset
uspto-grants-1999_05
Patent number
US05902803

Reaction notes

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