4-Chloroaniline → HCID 6326419, compound

HRID 49896Notes

Reaction equation

HRID 49896 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl.C(N(CC)CC)C.[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.[CH3:31][C:32]1[CH:37]=[C:36]([CH2:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42](=O)[NH:41][N:40]=2)[CH:35]=[CH:34][N:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CO>[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:42]2[C:43]3[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:39]([CH2:38][C:36]3[CH:35]=[CH:34][N:33]=[C:32]([CH3:31])[CH:37]=3)=[N:40][N:41]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 78124-ChloroanilineHCID 10340Sodium CarbonateHCID 11130Triethylamine hydrochlorideHCID 14812Phosphorus oxide (P4O10)HCID 10777138HCID 10777138, compound

Product 1

HCID 6326419HCID 6326419, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 910 mg (6.36 mmol) phosphorus pentoxide, 876 mg (6.36 mmol) triethylamine hydrochloride, and 812 mg (6.36 mmol) 4-chloroaniline is heated at 200° C. until a homogeneous melt has formed. To the melt, 400 g (1.59 mmol) 4-[(2-methyl-pyridin-4-yl)-methyl]-1(2H)-phthalazinone is added and the reaction mixture stirred for a further 16 h at 200° C. The cooled reaction mixture is distributed with thorough stirring and use of an ultrasonic bath between a dichloromethane/methanol mixture (about 20:1) and saturated aqueous sodium carbonate solution. The organic phase washed with water and brine is dried over anhydrous sodium sulfate, evaporated under vacuum, and the residue purified by means of flash chromatography on silica gel with particle size 0.04-0.06 mm, using an acetate/methanol mixture (19:1). Title compound is obtained after evaporation of the product-containing fractions under vacuum and crystallization of the residue from acetonitrile; m.p. 158-159° C.; ESI-MS: (M+H)+=361. The starting material is prepared as follows:

Workup

  1. customhas formed
  2. customThe cooled reaction mixture
  3. stirringwith thorough stirring
  4. washThe organic phase washed with water and brine
  5. dry with materialis dried over anhydrous sodium sulfate
  6. customevaporated under vacuum
  7. customthe residue purified by means of flash chromatography on silica gel with particle size 0.04-0.06 mm

Sources & evidence

ORD record
ord-16b3b8617bca4dd182de9a05e435f45d
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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