Ethanol → HCID 178470464, compound

HRID 1658748Notes

Reaction equation

HRID 1658748 reaction equation
C(OC(=O)[C:5](=[CH:11][NH:12][C:13]1[N:17]([CH2:18][CH3:19])[N:16]=[CH:15][CH:14]=1)[C:6]([O:8]CC)=O)C.[CH2:21]([OH:23])[CH3:22].[C:24]1([O:30]C2C=CC=CC=2)C=CC=CC=1>>[CH2:21]([O:23][C:24]([C:15]1[C:14]2[C:13](=[N:12][CH:11]=[CH:5][C:6]=2[OH:8])[N:17]([CH2:18][CH3:19])[N:16]=1)=[O:30])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 7583Diphenyl EtherHCID 12845080Diethyl {[(1-ethyl-1H-pyrazol-5-yl)amino]methylene}malonate

Product 1

HCID 178470464HCID 178470464, compound

Procedure

253 g of [[(1-ethyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester (0.09 mol) is dissolved in 770 g of diphenyl ether. The reaction mixture is heated to 235°-250° (bath temperature) and allowed to react at this temperature for 1 to 2 hours, while the resulting ethanol is continuously distilled off. The remaining alcohol is removed by means of a water aspirator. The diphenyl ether is separated by distillation with a fractionating column in vacuo. The 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridinecarboxylic acid ethyl ester is obtained at b.p. 0.05 115°-120°, yield 195 g = 92% of theory, m.p. 85°-87°. The compound is recrystallized from ligroin (90° to 100°), and has a melting point of 87°-89°.

Workup

  1. temperatureThe reaction mixture is heated to 235°-250° (bath temperature)
  2. distillationis continuously distilled off
  3. customThe remaining alcohol is removed by means of a water aspirator
  4. customThe diphenyl ether is separated by distillation with a fractionating column in vacuo

Sources & evidence

ORD record
ord-dce576d2b9cd4d88827053fa35ce1b31
Source dataset
uspto-grants-1976_06
Patent number
US03966746

Reaction notes

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