Ethanolamine → HCID 20040899, compound

HRID 1762435Notes

Reaction equation

HRID 1762435 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][NH:11][C:3]=12.[CH2:18]([CH2:20][NH2:21])[OH:19]>C1(C)C(C)=CC=CC=1>[OH:19][CH2:18][CH2:20][NH:21][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][NH:11][C:3]=12

Participants

4

Reactant 2

HCID 700EthanolamineHCID 178426078HCID 178426078, compound

Product 1

HCID 20040899HCID 20040899, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 7-chloro-5-methyl-3-phenyl-1H-pyrazolo[4,3-b]pyridine (D9) (0.63 g) in xylene (15 ml) with ethanolamine (1.5 ml) was heated at reflux for 3 days under nitrogen. The solvent was then removed under reduced pressure and the residue dissolved in water with the minimum amount of methanol with warming. This solution was brought to pH9 by addition of 10% sodium hydroxide and then further diluted with water. The resulting emulsion was left to stand overnight to give the title compound as a pale yellow crystalline solid which was collected, washed with water and dried under vacuum to afford the title compound (0.686 g, 95%), m.p. softening and partial melting at 135° with resolidification and melting at 186°-188°. (Found: C, 64.58; H, 6.42; N, 20.06. C15H16N4O.1/2H2O requires C, 64.96; H, 6.18; N, 20.20%).

Workup

  1. temperatureat reflux for 3 days under nitrogen
  2. customThe solvent was then removed under reduced pressure
  3. dissolutionthe residue dissolved in water with the minimum amount of methanol
  4. temperaturewith warming
  5. additionThis solution was brought to pH9 by addition of 10% sodium hydroxide
  6. additionfurther diluted with water
  7. waitThe resulting emulsion was left

Sources & evidence

ORD record
ord-de5705df418f43568323da8d08ac3cbe
Source dataset
uspto-grants-1989_05
Patent number
US04833136

Reaction notes

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