Phosphorus oxychloride → Methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate

HRID 2357647Notes

Reaction equation

HRID 2357647 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.P(Cl)(Cl)([Cl:25])=O>C(#N)C>[Cl:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178497700HCID 178497700, compound

Product 1

HCID 77230175Methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-(1-hydroxyphthalazin-6-yl)-4-methylbenzoate (2.85 g, 9.68 mmol) was suspended in acetonitrile (19.4 mL), cooled to 0° C. to which phosphorus oxychloride (1.81 mL, 19.4 mmol) was added dropwise. The reaction mixture was warmed to 80° C. for 2.5 h, then concentrated, diluted with 150 mL of ethyl acetate, added to a separatory funnel and partitioned with water. The organics were washed 2×50 mL with water, separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. MS (ES+): 313(M+H)+.

Workup

  1. additionwas added dropwise
  2. concentrationconcentrated
  3. additiondiluted with 150 mL of ethyl acetate
  4. additionadded to a separatory funnel
  5. custompartitioned with water
  6. washThe organics were washed 2×50 mL with water
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ba2a5c4a8964645b3741049c3d9981d
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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