Phosphorus oxychloride → HCID 18186440, compound

HRID 1357469Notes

Reaction equation

HRID 1357469 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=O)[NH:16][N:15]=[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]=2[N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:28])=O>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]([N:25]=1)=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[N:15]=[N:16][C:17]=2[Cl:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11544453HCID 11544453, compound

Product 1

HCID 18186440HCID 18186440, compound

Procedure

2-Benzyloxy-8-phenyl-6H-pyrido[2,3-d]pridazin-5-one (845 mg) was stirred in phosphorus oxychloride (30 ml) at reflux for 4 h. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel, eluting with ethyl acetate, yielding 2-benzyloxy-5-chloro-8-phenylpyrido[2,3-d]pyridazine as a pale yellow solid (950 mg). 1H NMR (400 MHz, DMSO) δ5.50 (2H, s), 7.35 (5H, m), 7.58 (3H, m), 7.65 (1H, d, J=9.0 Hz), 8.06 (2H, m), 8.60 (1H, d, J=9.0 Hz); MS (ES+) m/e 348, 350 [MH]+.

Workup

  1. temperatureat reflux for 4 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography on silica gel
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-dfd52f263a88469cbc7bfc69e12180b3
Source dataset
uspto-grants-2003_07
Patent number
US06593325B1

Reaction notes

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