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

HRID 2357534Notes

Reaction equation

O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.P(Cl)(Cl)([Cl:26])=O>C(#N)C>[Cl:26][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Ethyl 3-(1-hydroxyphthalazin-6-yl)-4-methylbenzoate (5.5 g) was suspended in acetonitrile (50 mL), and was treated with phosphorus oxychioride (3 mL, 36 mmol). The mixture was stirred at 90° C. for 4 h. The mixture was concentrated to remove all solvent, and redissolved in ethyl acetate (200 mL). The organic solution was washed with water (3×20 mL), brine (20 mL), and was dried over anhydrous Na2SO4, and concentrated in vacuo to give ethyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate as a pale yellow solid.

Workup

concentrationThe mixture was concentrated
customto remove all solvent
dissolutionredissolved in ethyl acetate (200 mL)
washThe organic solution was washed with water (3×20 mL), brine (20 mL)
dry with materialwas dried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8784c54744ab47778f47e0f493b07398
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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