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

HRID 448921Notes

Reaction equation

HRID 448921 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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), δ, 8.82 (1H, s), 7.83-7.92 (2H, m), 7.33-7.41 (1H, m).

Workup

  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

Sources & evidence

ORD record
ord-437ef2d8335646d586fc9323653ea0ed
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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