Phosphorus oxychloride → 4-Chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile

HRID 612147Notes

Reaction equation

HRID 612147 reaction equation
O[C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].P(Cl)(Cl)([Cl:22])=O>CN(C)C=O>[Cl:22][C:2]1[C:11]2[C:6](=[C:7]([O:16][CH3:17])[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486763HCID 178486763, compound

Product 1

HCID 224666114-Chloro-6,7,8-trimethoxy-3-quinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A stirred mixture of 1.30 g of 4-hydroxy-6,7,8-trimethoxy-quinoline-3-carbonitrile, 10 ml of phosphorous oxychloride, and 1 drop of N,N-dimethylformamide was refluxed for 10 minutes and evaporated free of volatile matter. The residue was stirred with 20 ml of 5% methyl alcohol in ethyl acetate. The product was collected and dried to give 1.12 g of 4-chloro-6,7,8-trimethoxy-quinoline-3-carbonitrile as a solid, mp 161-163° C.; mass spectrum (EI, m/e): M 278.0452.

Workup

  1. temperaturewas refluxed for 10 minutes
  2. customevaporated free of volatile matter
  3. customThe product was collected
  4. customdried

Sources & evidence

ORD record
ord-925ef53ab7b64e0f8a5bc246f0ad4d50
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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