Acetate → HCID 9818750, compound

HRID 49880Notes

Reaction equation

HRID 49880 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1.C([O-])(=O)C>C(=O)([O-])[O-].[K+].[K+]>[CH3:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 175AcetateHCID 7813p-ToluidineHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 9818750HCID 9818750, compound

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.384 g (1.5 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 0.482 g (4.5 mmol) p-toluidine is stirred for 1.5 h at 90° C. under a nitrogen atmosphere. The reaction mixture is then distributed between 30 ml acetate and 20 ml of 20% aqueous potassium carbonate solution. The organic phase washed with water and dried over anhydrous sodium sulfate is evaporated and the residue purified on silica gel by flash chromatography using acetate/methanol mixtures (50:1 to 9:1). Title compound is obtained after crystallization of the product-containing fractions from acetonitrile and drying under HV; m.p. 152-153° C.; ESI-MS: (M+H)+=327.

Workup

  1. washThe organic phase washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customis evaporated
  4. customthe residue purified on silica gel by flash chromatography

Sources & evidence

ORD record
ord-0ee547c4878842c0b4af4db53c2fdb6f
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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