Phosphorus oxychloride → HCID 57420585, compound

HRID 1713146Notes

Reaction equation

HRID 1713146 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13](O)[N:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:21].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([Cl:21])[N:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178515393HCID 178515393, compound

Product 1

HCID 57420585HCID 57420585, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a slurry of 7-benzyl-5,6,7,8-tetrahydropyrido[3,4-c]pyridazin-3-ol (7 g, 29.1 mmol) in toluene (50 ml) is added POCl3 (7 ml). The resulting mixture is heated at 85° C. for 3 hr. The mixture is cooled to 0° C. and is neutralized with saturated NaHCO3 solution. The mixture is extracted with EtOAc (100 ml×2). The combined organic phase is dried over sodium sulfate, and the solvent is removed under reduced pressure to give a residue that is purified by silica gel chromatography (EtOAc/4% TEA) to give the title compound.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. extractionThe mixture is extracted with EtOAc (100 ml×2)
  3. dry with materialThe combined organic phase is dried over sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customto give a residue that
  6. customis purified by silica gel chromatography (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-f2ff58a89ca148a5bcb34593a97ed8cf
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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