4-Chloroaniline → N-(4-chlorophenyl)-4-[1-(pyridin-4-yl)ethyl]phthalazin-1-amine

HRID 49899Notes

Reaction equation

HRID 49899 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=O)[NH:11][N:10]=2)[CH3:8])=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl.C(N(CC)CC)C.[Cl:42][C:43]1[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=1>ClCCl.CO>[Cl:42][C:43]1[CH:49]=[CH:48][C:46]([NH:47][C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]([CH:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH3:8])=[N:10][N:11]=2)=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 11130Triethylamine hydrochlorideHCID 14812Phosphorus oxide (P4O10)HCID 10538706rac4-[1-(4-pyridyl)ethyl]-1(2H)-phthalazinone

Product 1

HCID 6326422N-(4-chlorophenyl)-4-[1-(pyridin-4-yl)ethyl]phthalazin-1-amine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 300 mg (1.19 mmol) rac 4-[1-(4-pyridyl)ethyl]-1(2H)-phthalazinone, 683 mg (4.77 mmol) phosphorus pentoxide, 657 mg (4.77 mmol) triethylamine hydrochloride, and 609 mg (4.77 mmol) 4-chloroaniline is heated for 8 h to 205° C. The brown solution is taken up in dichloromethane/methanol 19:1, washed successively with sat. Na2CO3 solution, 3× with water and brine, and the organic phase (Na2O4) is washed and concentrated by evaporation. Chromatography (SiO2; ethyl acetate/CH3OH, 19:1) yields the title compound: m.p.: 132-134° C.; Anal. calc.(C21H17N4Cl.½CH3OH) C, 68.52%; H, 5.08%; N, 14.87%. found. C, 68.4%; H, 5.0%; N, 14.9%.

Workup

  1. temperatureis heated for 8 h to 205° C
  2. washwashed successively with sat. Na2CO3 solution, 3× with water and brine
  3. washthe organic phase (Na2O4) is washed
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1966a47c283b44e685e6d94508d37553
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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