Ethanol → HCID 13118503, compound

HRID 850914Notes

Reaction equation

HRID 850914 reaction equation
[NH2:1][C:2]1[C:8](O)=[CH:7][C:6](=[O:10])[CH:5]=[CH:4][CH:3]=1.C(O[CH:14]=[C:15]([C:21]([O:23]CC)=[O:22])[C:16]([O:18]CC)=[O:17])C.C([OH:28])C>>[OH:28][C:5]1[C:6](=[O:10])[CH:7]=[CH:8][C:2]([NH:1][CH:14]=[C:15]([C:21]([OH:23])=[O:22])[C:16]([OH:18])=[O:17])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6871Diethyl (ethoxymethylene)malonateHCID 20503426HCID 20503426, compound

Product 1

HCID 13118503HCID 13118503, compound

Procedure

A mixture of 5-amino-6-hydroxy-2,4,6-cycloheptatrien-1-one (5.76 g), described by T. Nozoe et al., Proc. Japan Acad., 27, 188 (1951), and diethyl ethoxymethylenemalonate (15.2 g) was heated at 140° C. for 2 hr. The reaction mixture was cooled and dissolved in ethanol. The resulting crystalline precipitate was collected, treated with charcoal in a chloroform solution and the recrystallized from ethanol to give 4.76 g of 2-[(4-hydroxy-5-oxo-1,3,6-cycloheptatriene-1-yl)aminomethylene]propanedioic acid (V; R7 =OH and R8 =C2H5), mp 175°-176° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe resulting crystalline precipitate was collected
  3. additiontreated with charcoal in a chloroform solution
  4. customthe recrystallized from ethanol

Sources & evidence

ORD record
ord-144f596501764b4ab67dc7783bb54f5a
Source dataset
uspto-grants-1983_05
Patent number
US04382088

Reaction notes

Loading…