Phosphorus oxychloride → HCID 22267327, compound

HRID 488727Notes

Reaction equation

HRID 488727 reaction equation
[CH3:1][C:2]1[C:11](C(O)=O)=[C:10](O)[C:9]2[C:4](=[C:5]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[N:6]=[CH:7][CH:8]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:26].C([O-])(O)=O.[Na+]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[CH:11]=[C:10]([Cl:26])[C:9]2[C:4](=[C:5]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[N:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178432047HCID 178432047, compound

Product 1

HCID 22267327HCID 22267327, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
230 °C

Procedure

A solution of 2-methyl-3-carboxy-4-hydroxy-8-(2′,4′-dichlorophenyl)-1,7-naphthyridine (0.41 g, 1.2 mmole) in diphenyl ether (0.4 ml) is stirred and heated to 230° C. for 1.5 h. The solution is allowed to cool to r.t., and POCl3 (0.8 ml) is added. This mixture is heated to 100° C. for 2 h, then allowed to cool to r.t., and poured into 5% NaHCO3. This is extracted with EtOAc, the organic phase washed with brine, dried and concentrated. The product is purified by flash chromatography on silica gel to give the title compound D7.

Workup

  1. temperatureto cool to r.t.
  2. temperatureThis mixture is heated to 100° C. for 2 h
  3. temperatureto cool to r.t.
  4. extractionThis is extracted with EtOAc
  5. washthe organic phase washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-6ae2807e5bcf49429b7de78d6fc2fc4c
Source dataset
uspto-grants-2005_12
Patent number
US06974808B2

Reaction notes

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