Nitrogen → 1-Chloro-6-methoxyphthalazine

HRID 2268828Notes

Reaction equation

HRID 2268828 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[NH:8][N:7]=[CH:6]2.N#N.P(Cl)(Cl)([Cl:18])=O>C(#N)C>[Cl:18][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[N:7][N:8]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 24813Phosphorus oxychlorideHCID 122985436-Methoxyphthalazin-1-ol

Product 1

HCID 183816081-Chloro-6-methoxyphthalazineYield 98.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 6-methoxy-2H-phthalazin-1-one (6.4 g, 36.3 mmoles), prepared as described in example 3, in acetonitrile (65 ml) under stirring and dry N2 at room temperature, was dropwise added with phosphorous oxychloride (6.8 ml, 73 mmoles), then the mixture was refluxed. After 3 hours the mixture was concentrated, taken up in water, neutralised with NaHCO3 and extracted more times with CH2Cl2. The organic phases were washed with water, anhydrified and concentrated to give 6.94 g of the title compound (yield: 98.3%). m.p.: 181-183° C.

Workup

  1. customprepared
  2. temperaturethe mixture was refluxed
  3. concentrationAfter 3 hours the mixture was concentrated
  4. extractionextracted more times with CH2Cl2
  5. washThe organic phases were washed with water, anhydrified
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-29f621a189f4445b9ecb0371d7a99b92
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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