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

HRID 912063Notes

Reaction equation

HRID 912063 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:8][NH2:9])=[CH:6][CH:7]=1.[C:10](O)(=O)[CH2:11][OH:12].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:4]([C:10]([CH2:11][OH:12])=[N:9][N:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 1007873-Chloro-6-hydrazinopyridazineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 50990671(6-Chloro-(1,2,4)triazolo(4,3-b)pyridazin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-chloro-6-hydrazinopyridazine (1.44 g, 9.96 mmol), glycolic acid (0.76 g, 10 mmol) and p-TsOH.H2O (2.37 g, 12.4 mmol) in toluene was refluxed overnight. Some oil formed at the bottom of the flask. LC-MS of this oil showed the desired product was formed. Toluene was decanted off, and the oil residue was suspended in water (10 mL), then basified with 3N aq. NaOH to pH=10, the resulting off-white solid was collected, and dried to give the title compound. LC-MS (ES+): 185/187 (3/1) [MH+]. 1H NMR (CDCl3): δ=2.96 (br s, 1H, —OH), 5.25 (s, 2H), 7.17 (d, J=9.6 Hz, 1H), 8.11 (d, J=9.6 Hz, 1H).

Workup

  1. temperaturewas refluxed overnight
  2. customSome oil formed at the bottom of the flask

Sources & evidence

ORD record
ord-2578ee1ab4ec4084bf871489bfbe939b
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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