Phosphorus oxychloride → 1-Chloro-8-methoxy-3-phenyl-2,7-naphthyridine

HRID 1034938Notes

Reaction equation

HRID 1034938 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=O)[NH:10][C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:8]2.O=P(Cl)(Cl)[Cl:22]>CC#N>[Cl:22][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[N:4][C:3]=2[O:2][CH3:1])[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 580937988-methoxy-3-phenyl-2,7-naphthyridin-1(2H)-one

Product 1

HCID 580943901-Chloro-8-methoxy-3-phenyl-2,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-Methoxy-3-phenyl-2,7-naphthyridin-1(2H)-one (80 mg, 0.32 mmol) is dissolved in CH3CN (2 mL) and POCl3 (59 uL, 0.64 mmol) The mixture is stirred at 80° C. for 3 hours. POCl3 is removed and neutralized with sat. NaHCO3. The compound is extracted with CHCl3 and the organic layer is dried (Na2SO4) and evaporated to yield the crude compound and used for the next step without any further purification. MS m/z 271.1 (M+1).

Workup

  1. customPOCl3 is removed
  2. extractionThe compound is extracted with CHCl3
  3. dry with materialthe organic layer is dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-c2338579ddce4133b2fbfd268eeb6ed6
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Reaction notes

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