Ammonium Acetate → HCID 18694017, compound

HRID 1603708Notes

Reaction equation

HRID 1603708 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]([N:17]1[CH:21]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:19]=[C:18]1[C:28]([O:30]CC)=O)[C:11]2=O)=[O:5])[CH3:2].C([O-])(=O)C.[NH4+:37]>C(O)(=O)C>[O:30]=[C:28]1[NH:37][C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[C:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:8]=3[CH2:9][C:10]=2[N:17]2[CH:21]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:19]=[C:18]12

Participants

4

Reactant 2

HCID 517165Ammonium Acetate2×HCID 18694018HCID 18694018, compound

Product 1

HCID 18694017HCID 18694017, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.63 g of ethyl 1-[4-(ethoxycarbonylmethyl)-1-oxoindan-2-yl]-4-(ethoxycarbonylmethyl)imidazole-2-carboxylate, 15 ml of acetic acid and 2.83 g of ammonium acetate is heated at reflux for 5 hours. The heating is stopped, 1.4 g of ammonium acetate are added and the refluxing is continued for 2 hours. The reaction mixture is poured over 100 ml of crushed ice and extracted with 3×50 ml of dichloromethane. The organic phase is dried over magnesium sulphate, filtered and evaporated in a rotary evaporator. The evaporation residue is suspended in 15 ml of ethyl acetate to give 0.8 g of diethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2,9-diacetate in the form of a beige solid [1H NMR spectrum in DMSO-d6, T=300K, δ in ppm, (250 MHz): 1.25 (6H, m, 2 CH3), 3.80 (4H, s, 2 CH2CO2Et), 4.00 (2H, s, CH2), 4.15 (4H, q, J=6 Hz 2 OCH2), 7.15 (1H, d, J=8 Hz, arom. CH), 7.40 (1H, t, J=8 Hz, arom. CH), 7.80 (1H, d, J=8 Hz, arom. CH), 7.90 (1H, s, arom. CH), 12.4 (1H, s, CONH)].

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 hours
  3. extractionextracted with 3×50 ml of dichloromethane
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-697398bd27d04c968d050c514049ecbd
Source dataset
uspto-grants-1999_11
Patent number
US05990108

Reaction notes

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