Phosphorus oxychloride → 4-Chloro-6-methoxy-1-pyridin-4-ylmethyl-phthalazine

HRID 2268928Notes

Reaction equation

HRID 2268928 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[N:8][NH:9][C:10]2=O)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:23]>C(#N)C>[Cl:23][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[C:7]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[N:8][N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 18381684HCID 18381684, compound

Product 1

HCID 121090714-Chloro-6-methoxy-1-pyridin-4-ylmethyl-phthalazineYield 23.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 7-methoxy-4-pyridin-4-ylmethyl-2H-phthalazin-1-one (11.4 g, 42.65 mmoles), prepared as described in example 130, and POCl3 (7.95 ml, 85.30 mmoles) in acetonitrile (110 ml) was refluxed for 1.5 hours. Further POCl3 (40 ml) was added and the reflux was kept on overnight. The mixture was dried, dissolved in water, neutralised with NaHCO3, extracted with CH2Cl2 and dried. The residue was chromatographed (eluent: CH2Cl2/CH3OH 97:3) to give 2.9 g of the title compound (yield: 23.8%).

Workup

  1. customprepared
  2. temperaturewas refluxed for 1.5 hours
  3. customThe mixture was dried
  4. dissolutiondissolved in water
  5. extractionextracted with CH2Cl2
  6. customdried
  7. customThe residue was chromatographed (eluent: CH2Cl2/CH3OH 97:3)

Sources & evidence

ORD record
ord-ef8c049b98084558af9be4b322cd1cad
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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