N,N-Dimethylaniline → HCID 86761428, compound

HRID 1663007Notes

Reaction equation

HRID 1663007 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=O)[NH:13][N:12]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:33].C([O-])(O)=O.[Na+]>[N+](CC)(CC)(CC)CC.[Cl-].C(#N)C>[Cl:33][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]([CH2:10][C:4]2[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=2)=[N:12][N:13]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 67215072HCID 67215072, compound

Product 1

HCID 86761428HCID 86761428, compound

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1.38 g (4.00 mMol) of 4-[5-bromo-6-methoxy-(pyridin-3-yl)-methyl]phthalazin-1(2H)-one and 1.33 g (8.0 mMol) of Et4NCl in 75 ml of acetonitrile under N2-atmosphere, 1.01 ml (8.0 mMol) of N,N-dimethyl-aniline and 8.79 ml (96 mMol) of POCl3 are added. After heating the mixture for 1 h to 90° C., the resulting solution is cooled to RT, pored into 400 ml of icewater and 500 ml sat. NaHCO3 solution and extracted with 3 portions of EtOAc. The organic phases are washed twice with water and brine, dried (Na2SO4) and concentrated to the title compound containing some 1-chloro-4-[5-bromo-6-hydroxy-(pyridin-3-yl)-methyl]phthalazine: FAB-MS: (M+H)+=364/366; HPLC(Grad20-100) tRet=14.5.

Workup

  1. temperatureAfter heating the mixture for 1 h to 90° C.
  2. extractionextracted with 3 portions of EtOAc
  3. washThe organic phases are washed twice with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to the title compound
  6. additioncontaining some 1-chloro-4-[5-bromo-6-hydroxy-(pyridin-3-yl)-methyl]phthalazine

Sources & evidence

ORD record
ord-d3af66d413b644e6870752d602276df0
Source dataset
uspto-grants-2011_10
Patent number
US08034814B2

Reaction notes

Loading…