Phosphorus oxychloride → 5-Chlorobenzo[c][2,6]naphthyridine-8-carbonitrile

HRID 2174888Notes

Reaction equation

HRID 2174888 reaction equation
P(Cl)(Cl)([Cl:3])=O.O=[C:7]1[C:16]2[C:11](=[CH:12][N:13]=[CH:14][CH:15]=2)[C:10]2[CH:17]=[CH:18][C:19]([C:21]#[N:22])=[CH:20][C:9]=2[NH:8]1>>[Cl:3][C:7]1[C:16]2[C:11](=[CH:12][N:13]=[CH:14][CH:15]=2)[C:10]2[CH:17]=[CH:18][C:19]([C:21]#[N:22])=[CH:20][C:9]=2[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 509421405-Oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carbonitrile

Product 1

HCID 509421465-Chlorobenzo[c][2,6]naphthyridine-8-carbonitrile

Procedure

Phosphorus oxychloride (2 mL) was added to the 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carbonitrile (150 mg, 0.66 mmol). The mixture was heated reflux for 3 hours at which time LCMS analysis indicated the absence of any starting material. Volatiles were removed under vacuum and the crude product was dissolved in dichloromethane, washed with brine and saturated aqueous sodium bicarbonate and dried over sodium sulfate. After concentrating under vacuum, the crude product was triturated with ethyl acetate and hexanes to give 5-chlorobenzo[c][2,6]naphthyridine-8-carbonitrile (125 mg). LCMS (ESI) 240.3 (M+1)+.

Workup

  1. temperatureThe mixture was heated
  2. temperaturereflux for 3 hours at which time LCMS analysis
  3. customVolatiles were removed under vacuum
  4. dissolutionthe crude product was dissolved in dichloromethane
  5. washwashed with brine and saturated aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentrating under vacuum
  8. customthe crude product was triturated with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-edb92bccb5e8402492f4a48f428606f7
Source dataset
uspto-grants-2015_06
Patent number
US09062043B2

Reaction notes

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