Acetic Acid → HCID 86754834, compound

HRID 1870808Notes

Reaction equation

HRID 1870808 reaction equation
[CH2:1]([O:3][C:4](/[CH:6]=[CH:7]/[C:8]1[N:9]=[C:10]([C:29](OCC)=[O:30])[N:11]([C:13]2(CC(OCC)=O)[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=O)[CH:12]=1)=[O:5])[CH3:2].[C:34]([OH:37])(=[O:36])[CH3:35].C([O-])(=O)C.[NH4+:42]>O>[C:34]([CH2:35][C:15]1[C:20]2[CH2:21][C:13]3[N:11]4[CH:12]=[C:8](/[CH:7]=[CH:6]/[C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:9]=[C:10]4[C:29](=[O:30])[NH:42][C:14]=3[C:19]=2[CH:18]=[CH:17][CH:16]=1)([OH:37])=[O:36]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 86754835HCID 86754835, compound

Product 1

HCID 86754834HCID 86754834, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.3 g of ethyl (E)-4-(2-ethoxycarbonylvinyl)-1-(ethoxycarbonylmethyl-1-oxoindan-2-yl)imidazole-2-carboxylate, 7 ml of acetic acid and 5 g of ammonium acetate is heated at reflux for 1 hour. The reaction mixture is supplemented with 7 ml of distilled water and the insoluble matter is isolated by filtration, washed with 2×5 ml of distilled water and then 2×5 ml of acetone. After drying under vacuum (1 mm Hg, 0.13 kPa) at about 20° C., 0.15 g of ethyl (E)-3-(9-carboxymethyl-4-oxo-5,10-dihydroimidazo[1,2-a]indeno[1,2-e]pyrazin-2-yl)acrylate is obtained in the form of a brown solid melting above 260° C., used as is in the subsequent syntheses [1H NMR spectrum in DMSO-d6, T=300K, δ in ppm (250 MHz): 1.22 (3H, t, J=6 Hz, CH3), 1.30 3H, t, J=6 Hz, CH3), 3.87 (2H, s, CH2), 4.00 (2H, s, CH2), 4.15 (2H, q, J=6 Hz, OCH2), 4.25 (2H, q, J=6 Hz, OCH2), 6.70 (1H, d, J=16 Hz, ethylenic CH), 7.28 (1H, d, J=7 Hz, arom. CH), 7.42 (1H, t, J=7 Hz, arom. CH), 7.70 (1H, d, J=16 Hz, ethylenic CH), 7.84 (1H, d, J=7 Hz, arom. CH), 8.40 (1H, s, imidazole CH), 12.00 (1H, broad s, NHCO)].

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. customthe insoluble matter is isolated by filtration
  4. washwashed with 2×5 ml of distilled water
  5. customAfter drying under vacuum (1 mm Hg, 0.13 kPa) at about 20° C.

Sources & evidence

ORD record
ord-38d1de1e50cf453ca368d7d01a8c99fa
Source dataset
uspto-grants-2000_08
Patent number
US06100264

Reaction notes

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