Ethanolamine → HCID 178428526, compound

HRID 1762433Notes

Reaction equation

HRID 1762433 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[C:13]([CH3:16])=[N:14][NH:15][C:7]=12>C1(C)C(C)=CC=CC=1>[OH:2][CH2:1][CH2:3][NH:4][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[C:13]([CH3:16])=[N:14][NH:15][C:7]=12

Participants

4

Reactant 2

HCID 700EthanolamineHCID 178426080HCID 178426080, compound

Product 1

HCID 178428526HCID 178428526, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of ethanolamine (1.0 g, 0.016 mole) and 7-chloro-3,5-dimethyl-1H-pyrazolo[4,3-b]pyridine (1.0 g) in dry xylene (20 ml) was heated under reflux for 48 h. After cooling, the brown oil in the reaction vessel solidified. The solvent was then decanted off and the solid washed several times with xylene. The brown solid was dissolved in aqueous methanol and the pH adjusted to pH 8-9 with 10% sodium carbonate solution. The resulting solid was filtered off, dried and recrystallised from chloroform/methanol to give the title compound as a white solid (0.750 g, 71%), m.p. 225°-230° C. (Found: C, 58.29; H, 6.89; N, 27.06. C10H14N4O requires C, 58.18; H, 6.84; N, 27.17%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 h
  3. temperatureAfter cooling
  4. customThe solvent was then decanted off
  5. washthe solid washed several times with xylene
  6. dissolutionThe brown solid was dissolved in aqueous methanol
  7. filtrationThe resulting solid was filtered off
  8. customdried
  9. customrecrystallised from chloroform/methanol

Sources & evidence

ORD record
ord-48674b9c7dad4f5db948dc5f883938d7
Source dataset
uspto-grants-1989_05
Patent number
US04833136

Reaction notes

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