Phosphorus oxychloride → 2-Chloro-7-methylquinoline-6-carbonitrile

HRID 1465736Notes

Reaction equation

HRID 1465736 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=O)[NH:9]2)=[CH:4][C:3]=1[C:13]#[N:14].O=P(Cl)(Cl)[Cl:17]>O>[Cl:17][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[C:3]([C:13]#[N:14])[CH:4]=2)[N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 916190707-Methyl-2-oxo-1,2-dihydroquinoline-6-carbonitrile

Product 1

HCID 895253462-Chloro-7-methylquinoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7-Methyl-2-oxo-1,2-dihydroquinoline-6-carbonitrile (10 g, 54 mmol) and POCl3 (30 mL) was stirred at 110° C. for 2 h and then at 20° C. overnight. The mixture was carefully poured into a mixture of water and ice (400 mL) while being stirred vigorously. The product was collected by filtration and dried by co-evaporation with MeCN/Toluene to furnish the title product. LC/MS (IE, m/z): [M+1]+=203.

Workup

  1. customat 20° C.
  2. customovernight
  3. stirringwhile being stirred vigorously
  4. filtrationThe product was collected by filtration
  5. dry with materialdried by co-evaporation with MeCN/Toluene

Sources & evidence

ORD record
ord-4a4022605f1f4ce88a491fccf5cbfe8f
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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