Diphenyl Ether → HCID 178479973, compound

HRID 259401Notes

Reaction equation

HRID 259401 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][CH:8]=[C:9]2[C:14](=[O:15])[CH:13]=[CH:12][CH:11]=[C:10]2[CH2:16][CH2:17]C(OCC)=O)=[N:3]1.[C:23]1([O:29]C2C=CC=CC=2)C=CC=CC=1>>[OH:29][C:23]1[C:5]2[C:4](=[N:3][N:2]([CH3:1])[CH:6]=2)[N:7]=[CH:8][C:9]=1[C:14]([C:13]1[CH:12]=[CH:11][CH:10]=[CH:16][CH:17]=1)=[O:15]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 178470928HCID 178470928, compound

Product 1

HCID 178479973HCID 178479973, compound

Procedure

310 g. of 2-[[(1-methyl-1H-pyrazol-3-yl)amino]methylene]-3-oxobenzenepropanoic acid, ethyl ester (1.04 mol.) are heated with stirring for 15 minutes at 250° in 1 liter of diphenyl ether, while the alcohol formed is continuously distilled off. The solution is cooled and the diphenyl ether removed in vacuo. The residue is crystallized with methanol to obtain (4-hydroxy-2-methyl-2H-pyrazolo[3,4-b]-pyridin-5-yl)phenylmethanone, yield 156 g. (59.2%); m.p. 286°-290° (DMF).

Workup

  1. customformed
  2. distillationis continuously distilled off
  3. temperatureThe solution is cooled
  4. customthe diphenyl ether removed in vacuo
  5. customThe residue is crystallized with methanol

Sources & evidence

ORD record
ord-6ecf4534b59b4df59ff7c4fdf44fe232
Source dataset
uspto-grants-1977_07
Patent number
US04038281

Reaction notes

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