Methylhydrazine → Phenol, 2,6-bis(1,1-dimethylethyl)-4-(1-methyl-1H-pyrazolo(3,4-b)pyridin-3-yl)-

HRID 1382880Notes

Reaction equation

HRID 1382880 reaction equation
Cl[C:2]1[N:24]=[CH:23][CH:22]=[CH:21][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:9]([OH:16])=[C:8]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:7]=1)=O.[CH3:25][NH:26][NH2:27]>N1C=CC=CC=1>[C:17]([C:8]1[CH:7]=[C:6]([C:4]2[C:3]3[C:2](=[N:24][CH:23]=[CH:22][CH:21]=3)[N:26]([CH3:25])[N:27]=2)[CH:11]=[C:10]([C:12]([CH3:14])([CH3:13])[CH3:15])[C:9]=1[OH:16])([CH3:18])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 143682724-(2-Chloronicotinoyl)2,6-di-tertiary butylphenol

Product 1

HCID 3087379Phenol, 2,6-bis(1,1-dimethylethyl)-4-(1-methyl-1H-pyrazolo(3,4-b)pyridin-3-yl)-Yield 93.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 30 g of 4-(2-chloronicotinoyl)-2,6-di-tertiary butylphenol, 15 g of methylhydrazine and 150 ml of pyridine is reacted and treated in a similar manner as Example 1, and the obtained crude crystals are recrystallized from ethanol to give 27.3 g of 3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1-methyl-1H-pyrazolo[3,4-b]pyridine as white crystals, melting at 152°-154° C.

Workup

  1. customis reacted
  2. additiontreated in a similar manner as Example 1
  3. customthe obtained crude crystals
  4. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-310f0ae129bd4ccf880ef75584d665b7
Source dataset
uspto-grants-1989_02
Patent number
US04808620

Reaction notes

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