Phosphorus oxychloride → 1-Chloro-2,6-naphthyridine

HRID 2171002Notes

Reaction equation

HRID 2171002 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]1(=O)[C:15]2[C:10](=[CH:11][N:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][NH:7]1>ClC1C=CC=CC=1>[Cl:3][C:6]1[C:15]2[C:10](=[CH:11][N:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 8177432,6-Naphthyridin-1-ol

Product 1

HCID 128847741-Chloro-2,6-naphthyridine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

Under stirring, 184 ml (2.00 mol) phosphorus oxychloride was added slowly to a suspension of 146 g (1.00 mol) 2,6-naphthyridine-1(2H)-one in 1500 ml chlorobenzene at room temperature. The reaction mixture was heated to 100° C., stirred at this temperature for 16 hours and then cooled to room temperature. The solids were filtered off, washed with chlorobenzene and dried under vacuum. The residue was taken up in 1.5 l ice-cold water, 350 ml 50% aqueous sodium hydroxide solution to reach a pH value of 7-8. The precipitate thus formed was filtered off, washed with water and dried under vacuum yielding 1-chloro-[2,6]naphthyridine as brown crystals; HPLC/MS (A): 1.62 min, [M+H] 165.

Workup

  1. stirringstirred at this temperature for 16 hours
  2. temperaturecooled to room temperature
  3. filtrationThe solids were filtered off
  4. washwashed with chlorobenzene
  5. customdried under vacuum
  6. customThe precipitate thus formed
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-792bf86228b641bba182f892ba0d33eb
Source dataset
uspto-grants-2015_06
Patent number
US09051318B2

Reaction notes

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