Phosphorus oxychloride → HCID 22062921, compound

HRID 2187381Notes

Reaction equation

HRID 2187381 reaction equation
[CH:1]1([C:4]2[C:5](O)=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][N:8]=3)[CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:17]>CN(C=O)C>[Cl:17][C:5]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:13][C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517374HCID 178517374, compound

Product 1

HCID 22062921HCID 22062921, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of naphthyridine 4-4 (14 g, 77 mmol) and 100 mL POCl3 and 0.1 mL DMF was refluxed at 120° C. for 3 hr and concentrated. The residue was treated with 300 mL ice-water and solid K2CO3 until pH=9. The mixture was extracted with ethyl acetate (×3), washed with brine and dried over MgSO4. After solvent removal, the desired compound 4-5 was obtained as a yellowish solid.

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with 300 mL ice-water and solid K2CO3 until pH=9
  3. extractionThe mixture was extracted with ethyl acetate (×3)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customAfter solvent removal

Sources & evidence

ORD record
ord-a4496da19d9245d99860989ee5f26187
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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