Potassium Carbonate → 1-(4-Cyanoanilino)-4-(4-pyridylmethyl)phthalazine

HRID 49871Notes

Reaction equation

HRID 49871 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:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:24]([C:23]1[CH:26]=[CH:27][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)#[N:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133964-AminobenzonitrileHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 99496841-(4-Cyanoanilino)-4-(4-pyridylmethyl)phthalazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.384 g (1.5 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 0.532 g (4.5 mmol) 4-aminobenzonitrile is heated for 1.5 h at 90° C. The reaction mixture is then distributed between dichloromethane and 20% aqueous potassium carbonate solution. The organic phase washed with water and dried over sodium sulfate is evaporated and the residue purified on silica gel by flash chromatography using acetate/methanol mixtures (50:1 and). 25:1). Title compound is obtained after crystallization of the product-containing fractions from dichloromethane and drying under HV (8 h, 90° C.); m.p. 228-230° C.; ESI-MS: (M+H)+=338.

Workup

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

Sources & evidence

ORD record
ord-f2f95fd073184faf8e0ae02848eed4fe
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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