5-Chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine → 4-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

HRID 1678745Notes

Reaction equation

HRID 1678745 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]3OCC[O:19]3)=[CH:14][CH:13]=1)=[N:7]2>O1CCOCC1>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:6]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=1)=[N:7]2

Participants

3

Reactant 1

HCID 575007255-Chloro-2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-1,6-naphthyridine

Product 1

HCID 575007324-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-3 (5.0 g, 12.9 mmol) in 1,4-dioxane (30 mL) at 0° C. was added 8.5 mL of 3NHCl (25.7 mmol). The mixture was allowed to warm up to room temperature and stirred for 1.3 hr. The reaction was quenched by NaHCO3 (sat) until pF=7-8. The mixture was extracted by EtOAc (×3). The combined organic layers was washed with brine and dried over MgSO4 and concentrated to afford a yellow solid as the desired product A. LC/MS found: M+1=345.1

Workup

  1. customThe reaction was quenched by NaHCO3 (sat) until pF=7-8
  2. extractionThe mixture was extracted by EtOAc (×3)
  3. washThe combined organic layers was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2630c7c0e92e4ff086d48f6aa9058c8b
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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