Phosphorus oxychloride → 2-Chloro-5-fluoroquinoline-3-carbonitrile

HRID 661674노트

반응식

HRID 661674 반응식
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]#[N:14])[C:6](=O)[NH:7]2.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:6]1[C:5]([C:13]#[N:14])=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[F:1])[N:7]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 686018505-Fluoro-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

생성물 1

HCID 593703262-Chloro-5-fluoroquinoline-3-carbonitrile

실험 절차

5-Fluoro-2-oxo-1,2-dihydro-quinoline-3-carbonitrile (0.80 g, 4.3 mmol) was heated in POCl3 (10 mL) for 3 hrs. The mixture was concentrated and partitioned in ethyl acetate and water. The organic layer was separated, washed with NaHCO3, dried and concentrated. The residue was crystallized from a mixture of hexane and ethyl acetate to give 2-chloro-5-fluoro-quinoline-3-carbonitrile 32-1 as a white solid (0.83 g). 1HNMR (CDCl3), 6, 8.82 (1H, s), 7.83-7.92 (2H, m), 7.33-7.41 (1H, m).

후처리

  1. concentrationThe mixture was concentrated
  2. custompartitioned in ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with NaHCO3
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was crystallized from a mixture of hexane and ethyl acetate

출처 및 근거

ORD 기록
ord-8ceeb005195d438f86d90373025bcb94
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084614B2

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