Phosphorus oxychloride → 4-(4-Chloro-6-methoxy-phthalazin-1-yl)-butyric acid methyl ester

HRID 2297482Notes

Reaction equation

HRID 2297482 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10](=O)[NH:9][N:8]=1.O=P(Cl)(Cl)[Cl:23]>C(#N)C>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([Cl:23])=[N:9][N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12109280HCID 12109280, compound

Product 1

HCID 542691004-(4-Chloro-6-methoxy-phthalazin-1-yl)-butyric acid methyl esterYield 73.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-(6-methoxy-4-oxo-3,4-dihydro-phthalazin-1-yl)-butyric acid methyl ester (9.23 g, 0.034 moles), prepared as described in example 113, and POCl3 (1.87 ml, 0.2 mole) in acetonitrile (100 ml) was refluxed. After 1.5 hours the mixture was dried, taken up in water and neutralised with NaHCO3. The mixture was extracted with ethyl acetate and the organic phase dried to give a residue which was chromatographed (eluent: petrolatum/ethyl acetate 7:3). There were yielded 7.4 g of the title compound (yield: 63.9%).

Workup

  1. customprepared
  2. temperaturewas refluxed
  3. customAfter 1.5 hours the mixture was dried
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe organic phase dried
  6. customto give a residue which
  7. customwas chromatographed (eluent: petrolatum/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-ab710f49dc984807a5d167ad2eaa4696
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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