3-Chloroaniline → HCID 9798320, compound

HRID 1384098Notes

Reaction equation

HRID 1384098 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.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23]>C(=O)([O-])[O-].[K+].[K+]>[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH:23][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

Participants

4

Reactant 2

HCID 79323-Chloroaniline2×HCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 9798320HCID 9798320, compound

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.28 g (5 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 2.6 ml (25 mmol) 3-chloroaniline is stirred for 45 min at 90° C. under a nitrogen atmosphere. Excess 3-chloroaniline is then distlled off under HV at 60° C. and the residue distributed between 30 mldichloromethane and 20 ml of 20% aqueous potassium carbonate solution. The organic solution dried over anhydrous sodium sulfate is evaporated and the residue purified on silica gel by flash chromatography using acetate and acetate/methanol (20:1). The product-containing fractions are dissolved in 3 ml of methanol, and acidified with 2.3 ml 3N methanolic HCl, then ether is added while stirring until slight turbidity occurs, and the mixture is cooled to 0° C., resulting in the formation of a crystalline precipitate. After filtration, washing of the filter residue with ether, drying under HV (8 h, 110° C.) and equilibration for 65 h at 20° C. and in room atmosphere, the title compound is obtained with a water content of 7.3%; Smp. 233-236° C.; ESI-MS: (M+H)+=347.

Workup

  1. customis then distlled off under HV at 60° C.
  2. dry with materialThe organic solution dried over anhydrous sodium sulfate
  3. customis evaporated
  4. customthe residue purified on silica gel by flash chromatography
  5. dissolutionThe product-containing fractions are dissolved in 3 ml of methanol
  6. additionether is added
  7. stirringwhile stirring until slight turbidity
  8. temperaturethe mixture is cooled to 0° C.
  9. customresulting in the formation of a crystalline precipitate
  10. filtrationAfter filtration
  11. washwashing of the filter residue with ether
  12. customdrying under HV (8 h, 110° C.) and equilibration for 65 h at 20° C. and in room atmosphere

Sources & evidence

ORD record
ord-4fd4deae8fc042c0b7699e85d291954d
Source dataset
uspto-grants-2001_07
Patent number
US06258812B1

Reaction notes

Loading…