Phosphorus oxychloride → 4-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazine

HRID 2268857Notes

Reaction equation

HRID 2268857 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12](=O)[NH:11][N:10]=1.O=P(Cl)(Cl)[Cl:25]>C(#N)C>[Cl:25][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[C:9]([CH2:8][C:7]2[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=2[Cl:22])=[N:10][N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 224827114-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-one

Product 1

HCID 186292104-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazineYield 110.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-one (10 g, 25.5 mmoles), prepared as described in example 38, in acetonitrile (300 ml), was added with POCl3 (22.2 ml, 230 mmoles) and the mixture was refluxed. After 3 hours, the solution was concentrated, taken up in CH2Cl2, in water, and the pH was brought to 7-8 by Na2CO3. The organic phases were discoloured with charcoal, anhydrified and concentrated to give 10 g of the title compound (stoichiometric yield). m.p.: 156-166° C.

Workup

  1. customprepared
  2. temperaturethe mixture was refluxed
  3. concentrationthe solution was concentrated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-014f8b16e2b2465d9f4d4a56522545e6
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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