4-Chloroaniline → 1-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine hydrochloride

HRID 49859

Reaction equation

HRID 49859 reaction equation
[Cl:1][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.[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C(O)CCC>[ClH:1].[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][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:22][CH:21]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 98862921-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1.28 g (5 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine, 0.67 g (5.25 mmol) 4-chloroaniline and 15 ml 1-butanol is heated for 0.5 h at 100 h while stirring in a nitrogen atmosphere. The mixture is then cooled to RT, filtered, and the filtrate washed with 1-butanol and ether. For purification, the crystallizate is dissolved in 40 ml of hot methanol, the solution treated with activated carbon, filtered via Hyflo Super Cel, and the filtrate evaporated to about half its original volume, resulting in the formation of a crystalline precipitate. After cooling to 0° C., filtration, washing of the filter residue with ether, and drying under HV for 8 h at 130° C., the title compound is obtained; m.p. >270° C.; 1H NMR (DMSO-d6) 9.80-11.40 (br), 8.89-8.94 (m, 1H), 8.67 (d, 2H), 8.25-8.30 (m, 1H), 8.06-8.17 (m, 2H), 7.87 (d, 2H), 7.69 (d, 2H), 7.49 (d, 2H), 4.81 (s, 2H); ESI-MS: (M+H)+=347.

Workup

  1. temperatureis heated for 0.5 h at 100 h
  2. filtrationfiltered
  3. washthe filtrate washed with 1-butanol and ether
  4. customFor purification
  5. dissolutionthe crystallizate is dissolved in 40 ml of hot methanol
  6. additionthe solution treated with activated carbon
  7. filtrationfiltered via Hyflo Super Cel
  8. customthe filtrate evaporated to about half its original volume
  9. customresulting in the formation of a crystalline precipitate
  10. temperatureAfter cooling to 0° C.
  11. filtrationfiltration
  12. washwashing of the filter residue with ether
  13. customdrying under HV for 8 h at 130° C.

Sources & evidence

ORD record
ord-a9a371c157ff4e519c612c2e0a5f8130
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Linked notes

Loading…