Phosphorus oxychloride → HCID 50942238, compound

HRID 1919662Notes

Reaction equation

HRID 1919662 reaction equation
[CH:1]1[N:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[NH:5][C:6]2=O.P(Cl)(Cl)([Cl:18])=O>C(#N)C>[Cl:18][C:6]1[C:7]2[C:2](=[CH:1][N:10]=[CH:9][CH:8]=2)[C:3]2[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=2[N:5]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11586448HCID 11586448, compound

Product 1

HCID 50942238HCID 50942238, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzo[c][2,6]naphthyridin-5(6H)-one (1.0 eq, 813 mg, 4.15 mmol) was stirred in phosphorus oxychloride (5.0 eq, 2 ml, 21.84 mmol) and acetonitrile (10 ml). The mixture was stirred at reflux for 5 hours. The mixture was poured on ice, and the resulting solid filtered and dried. 5-chlorobenzo[c][2,6]naphthyridine was isolated as a grey solid (459 mg, 52% yield). LCMS (ES): 95% pure, m/z 215 [M+1]+.

Workup

  1. temperatureat reflux for 5 hours
  2. additionThe mixture was poured on ice
  3. filtrationthe resulting solid filtered
  4. customdried

Sources & evidence

ORD record
ord-38708b4172ed4268b2e44221f4681991
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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