Phosphorus oxychloride → 2-Chloro-6-(4-methylphenyl)-5-phenylnicotinonitrile

HRID 1354809Notes

Reaction equation

HRID 1354809 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[C:11]([C:15]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:12]1[N:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][C:11]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 211032106-(4-Methylphenyl)-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 211031982-Chloro-6-(4-methylphenyl)-5-phenylnicotinonitrile

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(4-methylphenyl)-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile (11-3) (5.73 g, 20.01 mmol) in POCl3 (50 mL) was heated to 100° C. overnight. Cooled and concentrated in vacuo. The residue was basified with sat. aqueous Na2CO3 solution and then extracted with CH2Cl2. The combined organic layers was dried, filtered and concentrated to give 2-chloro-6-(4-methylphenyl)-5-phenylnicotinonitrile (11-4) as a solid. LRMS m/z (M+H) Calcd: 305.1, found: 305.2.

Workup

  1. temperatureCooled
  2. concentrationconcentrated in vacuo
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layers was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-602b2216ebbd413e8177686fcea9732a
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

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