Ethanol → 4-Ethoxy-2-methyl-6-phenyl-2H-pyrazolo[3,4-b]pyridine

HRID 65992Notes

Reaction equation

HRID 65992 reaction equation
Cl[C:2]1[C:3]2[C:4](=[N:14][N:15]([CH3:17])[CH:16]=2)[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[Na].[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][C:2]1[C:3]2[C:4](=[N:14][N:15]([CH3:17])[CH:16]=2)[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 22756855HCID 22756855, compound

Product 1

HCID 227568624-Ethoxy-2-methyl-6-phenyl-2H-pyrazolo[3,4-b]pyridine

Procedure

8.5 g. of 4-chloro-2-methyl-6-phenyl-2H-pyrazolo[3,4-b]pyridine (0.035 mol.) are added to a solution of 0.9 g. of sodium (0.038 mol.) in 100 ml. of absolute ethanol. The mixture is heated at 150° in an autoclave for 5 hours. After cooling, the crystallized 4-ethoxy-2-methyl-6-phenyl2H-pyrazolo[3,4-b]pyridine is filtered off, washed with alcohol and then with water, yield: 6.2 g.; m.p. 170°-171°. An additional crop of 2.4 g. is obtained by evaporation of the mother liquor, total yield: 8.6 g. (97%). Recrystallization from ethanol gives a product of the melting point 171°-172°.

Workup

  1. temperatureThe mixture is heated at 150° in an autoclave for 5 hours
  2. temperatureAfter cooling
  3. filtrationthe crystallized 4-ethoxy-2-methyl-6-phenyl2H-pyrazolo[3,4-b]pyridine is filtered off
  4. washwashed with alcohol
  5. customis obtained by evaporation of the mother liquor, total yield: 8.6 g
  6. customRecrystallization from ethanol
  7. customgives a product of the melting point 171°-172°

Sources & evidence

ORD record
ord-f4317951d12c45a6a95a5810ef649016
Source dataset
uspto-grants-1978_12
Patent number
US04129738

Reaction notes

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