Phosphorus oxychloride → HCID 86607611, compound

HRID 2357557Notes

Reaction equation

HRID 2357557 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](O)=[N:12][N:11]=[CH:10]2.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:13]1[C:14]2[C:9](=[CH:8][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:18])=[CH:16][CH:15]=2)[CH:10]=[N:11][N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424144HCID 178424144, compound

Product 1

HCID 86607611HCID 86607611, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 6-o-tolylphthalazin-1-ol (3.65 g, 15 mmol) and phosphorus oxychloride (15 mL, 161 mmol) was stirred at 110° C. for 16 h. After cooling to RT, the phosphorus oxychloride was removed in vacuo. The residue was diluted with ethyl acetate (100 mL) and washed with saturated aqueous Na2O3 and brine. The organic solution was dried over magnesium sulfate, and concentrated under reduced pressure. Flash chromatography on silica gel (ethyl acetate: hexane 60:40) gave 1-chloro-6-o-tolylphthalazine as a yellow solid. MS (ESI, pos.ion) m/z: 255.0 (M+1)

Workup

  1. temperatureAfter cooling to RT
  2. customthe phosphorus oxychloride was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed with saturated aqueous Na2O3 and brine
  5. dry with materialThe organic solution was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45852ebac1e04f7f991a8e172c7df9a8
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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