Glycolic Acid → (6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanol

HRID 219064Notes

Reaction equation

HRID 219064 reaction equation
[C:1]1([C:7]2[N:12]=[N:11][C:10]([NH:13][NH2:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](O)(=O)[CH2:16][OH:17].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:15]([CH2:16][OH:17])=[N:14][N:13]=3)[N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 64098423-Hydrazinyl-6-phenylpyridazine

Product 1

HCID 57812703(6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(6-phenylpyridazin-3-yl)hydrazine (2.00 g, 10.7 mmol), glycolic acid (0.825 g, 10.8 mmol), p-TsOH.H2O (2.55 g, 13.4 mmol) in PhMe (50 mL) was refluxed for 14 h. PhMe was removed in vacuo. The resulting solids were diluted with water (30 mL). The mixture was brought to pH˜10 with 2N NaOH. The solids were isolated solid by filtration, washed with water and dried under vacuum to give an off white solid which was used without further purification. (ESI, pos. ion) m/z: 227.0 (M+H). Step 2.

Workup

  1. temperaturewas refluxed for 14 h
  2. customPhMe was removed in vacuo
  3. additionThe resulting solids were diluted with water (30 mL)
  4. customThe solids were isolated solid
  5. filtrationby filtration
  6. washwashed with water
  7. customdried under vacuum
  8. customto give an off white solid which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-9633fc792c714d56ad6a100e2e28612b
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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