Nitrogen → 1-Chloro-4-ethyl-6-methoxy-phthalazine

HRID 2297404Notes

Reaction equation

HRID 2297404 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6](=O)[NH:5][N:4]=1)[CH3:2].N#N.P(Cl)(Cl)([Cl:20])=O.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O>[Cl:20][C:6]1[C:7]2[C:12](=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[C:3]([CH2:1][CH3:2])=[N:4][N:5]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 183816114-ethyl-6-methoxy-2H-phthalazin-1-one

Product 1

HCID 183816451-Chloro-4-ethyl-6-methoxy-phthalazineYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-ethyl-6-methoxy-2H-phthalazin-1-one (1.3 g, 6.76 mmoles), prepared as described in example 9, in dry acetonitrile (20 ml), under stirring and dry N2 at room temperature, was added with phosphorous oxychloride (2.07 g, 13.52 mmoles). The mixture was refluxed and after 2 hours cooled, brought to small volume, taken up in water, added with Na2CO3 in excess and extracted three times with CH2Cl2. The organic phases were anhydrified and brought to dryness to give 1.34 g of the title compound (yield: 89%).

Workup

  1. customprepared
  2. temperatureThe mixture was refluxed and after 2 hours
  3. temperaturecooled
  4. extractionextracted three times with CH2Cl2

Sources & evidence

ORD record
ord-b4c04b0586874ccbaace943eea67512b
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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