5-Amino-2-hydroxy-2,4,6-cycloheptatrien-1-one → 2-(4-Hydroxy-5-oxo-1,3,6-cycloheptatrien-1-ylamino)-2-butenedioic Acid Diethyl Ester

HRID 66132

Reaction equation

HRID 66132 reaction equation
[C:1]([C:8]([O:10][CH2:11][CH3:12])=[O:9])#[C:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:13][C:14]1[CH:20]=[CH:19][C:18](=[O:21])[C:17]([OH:22])=[CH:16][CH:15]=1>C(O)C>[CH2:6]([O:5][C:3](=[O:4])[C:2]([NH:13][C:14]1[CH:20]=[CH:19][C:18](=[O:21])[C:17]([OH:22])=[CH:16][CH:15]=1)=[CH:1][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:7]

Participants

4

Reactant 2

HCID 234505-Amino-2-hydroxy-2,4,6-cycloheptatrien-1-oneHCID 69803Diethyl acetylenedicarboxylate

Product 1

HCID 867362102-(4-Hydroxy-5-oxo-1,3,6-cycloheptatrien-1-ylamino)-2-butenedioic Acid Diethyl Ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of diethyl acetylenedicarboxylate (183.5 g) and 5-amino-2-hydroxy-2,4,6-cycloheptatriene-1-one [147.5 g, described by T. Nozoe et al., Science Repts. Tokoku Univ., First ser., 35, 274(1952)] in ethanol (2,700 ml) is stirred at room temperature for 16 hours. The mixture is filtered and the precipitate is crystallized from ethanol to obtain crystals of the title compound, mp 108.5° C.

Workup

  1. filtrationThe mixture is filtered
  2. customthe precipitate is crystallized from ethanol

Sources & evidence

ORD record
ord-10aa283fe0b041468ebb0880110df018
Source dataset
uspto-grants-1978_12
Patent number
US04130649

Linked notes

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