Phosphorus oxychloride → 1-Chloro-N-(4-fluorophenyl)phthalazin-6-amine

HRID 454863Notes

Reaction equation

HRID 454863 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](O)=[N:14][N:13]=[CH:12]3)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:15]1[C:16]2[C:11](=[CH:10][C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:18][CH:17]=2)[CH:12]=[N:13][N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785189066-(4-Fluorophenylamino)phthalazin-1-ol

Product 1

HCID 866620921-Chloro-N-(4-fluorophenyl)phthalazin-6-amine

Conditions

Temperature
105 °C

Procedure

A mixture of 6-(4-fluorophenylamino)phthalazin-1-ol (0.650 g, 2.55 mmol) and phosphorus oxychloride (5.00 mL, 53.6 mmol) was heated at 105° C. in an oil bath for 2 h. The volatiles were removed by vacuum distillation. The residue was diluted with CH2Cl2 and treated with saturated aqueous solution of NaHCO3. The organic layer was collected and the aqueous layer was extracted with 25% i-PrOH/CHCl3 (2×). The combined organics were dried over Na2SO4, filtered through a pad of silica gel and eluted with EtOAc. The filtrate was concentrated to yield the title compound as a tan solid. MS (ESI, pos. ion) m/z: 274.0 (M+1).

Workup

  1. customThe volatiles were removed by vacuum distillation
  2. additionThe residue was diluted with CH2Cl2
  3. additiontreated with saturated aqueous solution of NaHCO3
  4. customThe organic layer was collected
  5. extractionthe aqueous layer was extracted with 25% i-PrOH/CHCl3 (2×)
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered through a pad of silica gel
  8. washeluted with EtOAc
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9352afc9c02644e0a7645135ed252db3
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Reaction notes

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