Phosphorus oxychloride → 3-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

HRID 2357685Notes

Reaction equation

HRID 2357685 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=3[CH3:21])[C:15]([OH:17])=O)=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.P(Cl)(Cl)([Cl:24])=O.[CH:27]1([NH2:30])[CH2:29][CH2:28]1>C([O-])(O)=O.[Na+].O>[Cl:24][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=3[CH3:21])[C:15]([NH:30][CH:27]3[CH2:29][CH2:28]3)=[O:17])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 69828CyclopropylamineHCID 178425877HCID 178425877, compound

Product 1

HCID 118483123-(1-chlorophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-(1-hydroxyphthalazin-6-yl)-4-methylbenzoic acid (1.08 g, 3.85 mmol) and phosphorus oxychloride (25.0 mL, 268 mmol) was heated to 105° C. for 3 h. After cooling to RT, the solvents were removed in vacuo. The residue was re-dissolved in CH2Cl2 and treated carefully with cyclopropylamine (1.36 mL, 19.3 mmol) at RT. The mixture was diluted with sat aq. NaHCO3 and H2O and extracted with CH2Cl2 (4×). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (MeOH/CH2Cl2=0→3%). Found MS (ESI, pos. ion) m/z: 338 (M+1).

Workup

  1. temperatureAfter cooling to RT
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was re-dissolved in CH2Cl2
  4. extractionextracted with CH2Cl2 (4×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-7e962fc9a0ab42c6ba11558b067a2899
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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