Phosphorus oxychloride → Methyl 5-chlorobenzo[c][2,6]naphthyridine-7-carboxylate

HRID 1919683Notes

Reaction equation

HRID 1919683 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2=[CH:12][CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:4]2[NH:3]1.P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2=[CH:12][CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:4]2[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 50941290Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxylate

Product 1

HCID 50941294Methyl 5-chlorobenzo[c][2,6]naphthyridine-7-carboxylateYield 92%

Procedure

Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxylate (1.0 eq, 85 mg, 0.334 mmol) was stirred in phosphorus oxychloride (2 ml) at 120° C. for 2 hours. The solvent was removed in vacuo. Ice and water were added. The resulting solid was filtered and dried to afford methyl 5-chlorobenzo[c][2,6]naphthyridine-7-carboxylate as a solid (84 mg, 92% yield). LCMS (ES): >95% pure, m/z 273 [M+1]+.

Workup

  1. customThe solvent was removed in vacuo
  2. additionIce and water were added
  3. filtrationThe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-2ac2a94f68d24311aa1f277943a7d049
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

Loading…