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

HRID 454863노트

반응식

HRID 454863 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
105 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9352afc9c02644e0a7645135ed252db3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497269B2

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