Phosphorus oxychloride → 4-Chloro-2,6-dihydro-2-methyl-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1-one

HRID 1835152Notes

Reaction equation

HRID 1835152 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=[C:5]2[C:4](=O)[NH:3]1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:4]1[C:5]2[C:6](=[CH:9][N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=2)[C:7](=[O:8])[N:2]([CH3:1])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 235032482,3-Dihydro-2-methyl-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1,4(6H)-dione

Product 1

HCID 235032554-Chloro-2,6-dihydro-2-methyl-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1-one

Procedure

A suspension of 2,3-dihydro-2-methyl-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazine-1,4(6H)-dione (0.10 g) in phosphorus oxychloride (1 ml) was heated at reflux for 30 minutes and then allowed to cool. The solvent was evaporated, water (25 ml) was added and the mixture was extracted with ethyl acetate (2×25 ml). The organic extracts were dried, filtered and evaporated to give the sub-title compound (0.095 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. temperatureto cool
  4. customThe solvent was evaporated
  5. additionwater (25 ml) was added
  6. extractionthe mixture was extracted with ethyl acetate (2×25 ml)
  7. customThe organic extracts were dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-04184055b5ba49aabe789d109fd45c87
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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