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

HRID 1060584Notes

Reaction equation

HRID 1060584 reaction equation
O=P(Cl)(Cl)[Cl:3].[Cl:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Cl:27])[C:12]=1[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[C:17](=O)[NH:16][N:15]=1>C(#N)C>[Cl:3][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)[C:14]([CH2:13][C:12]2[C:7]([Cl:6])=[CH:8][N:9]=[CH:10][C:11]=2[Cl:27])=[N:15][N:16]=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

POCl3 (22.2 ml, 230 mmoles) was added to a suspension of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-one (10 g, 25.5 mmoles), obtained as described in example 12, in acetonitrile (300 ml) and the mixture was heated under reflux. After 3 hours the solution was concentrated, taken up with CH2Cl2, with water, and the pH was brought to 7-8 with Na2CO3. The organic phases were decoloured with charcoal, dried and concentrated to give 10 g of the title compound (stoichiometric yield).

Workup

  1. customobtained
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. concentrationAfter 3 hours the solution was concentrated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e3ba75fa23cf42e995694098fa9cad9f
Source dataset
uspto-grants-2003_02
Patent number
US06525055B1

Reaction notes

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