Diphenyl Ether → HCID 178469631, compound

HRID 596758Notes

Reaction equation

HRID 596758 reaction equation
C(O[C:4](=[O:20])[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][CH2:9][CH3:10])=[O:7])C.C1(OC2C=CC=CC=2)C=CC=CC=1>C(O)C>[CH2:9]([O:8][C:6]([C:5]1[C:4]([OH:20])=[C:14]2[CH:15]=[N:16][N:17]([CH2:18][CH3:19])[C:13]2=[N:12][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

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

Product 1

HCID 178469631HCID 178469631, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

253 g. of [[(1-Ethyl-5-pyrazolyl)amino]methylene]malonic acid diethyl ester (0.09 mol.) are 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 1-2 hours while the resulting ethanol is continuously distilled off. The last amount of 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]pyridine-5-carboxylic 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 benzene (90° to 100°), m.p. 87°-89°.

Workup

  1. temperatureThe reaction mixture is heated to 235°-250° (bath temperature)
  2. distillationis continuously distilled off
  3. customThe last amount of 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-a611a73573d54e3abb63d3cfb1640ad8
Source dataset
uspto-grants-1977_03
Patent number
US04012373

Reaction notes

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