Acetyl chloride → HCID 136087647, compound

HRID 1382897Notes

Reaction equation

HRID 1382897 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>C(Cl)(Cl)Cl>[C:32]([N:18]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:24]2[C:16]([C:7]2[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]([OH:11])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=2)=[N:17]1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178440702HCID 178440702, compound

Product 1

HCID 136087647HCID 136087647, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 6.5 g of the compound of Example 1 in 50 ml of chloroform and 2.4 g of triethylamine is added dropwise 1.9 g of acetyl chloride over 15 minutes under cooling and stirring. After addition, the resulting mixture is stirred under cooling for 2 hours and then at room temperature for 3 hours. The reaction solution is washed with water, dried and then concentrated. The obtained residue is recrystallized from ethanol to give 5.7 g of 1-acetyl-3-(3,5-di-tertiary butyl-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine as oale yellow crvstals. melting at 169°-171° C.

Workup

  1. temperatureunder cooling
  2. additionAfter addition
  3. stirringthe resulting mixture is stirred
  4. temperatureunder cooling for 2 hours
  5. washThe reaction solution is washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe obtained residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-9be0e1e155274c0aac73966194536b91
Source dataset
uspto-grants-1989_02
Patent number
US04808620

Reaction notes

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