8-[4-(1,3-Dioxolan-2-yl)phenyl]9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine → 4-(9-Phenyl[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)benzaldehyde

HRID 1678740Notes

Reaction equation

HRID 1678740 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[CH:30][N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1>O1CCOCC1.Cl>[C:22]1([C:21]2[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][CH:10]=3)=[N:13][C:14]3[CH:15]=[CH:16][N:17]4[CH:30]=[N:29][N:28]=[C:18]4[C:19]=3[CH:20]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 594728818-[4-(1,3-Dioxolan-2-yl)phenyl]9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

Product 1

HCID 594729044-(9-Phenyl[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 8-[4-(1,3-dioxolan-2-yl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine (4-1, 0.80 g, 2.0 mmol) in dioxane (10 mL) and 3N HCl (10 mL) was stirred at room temperature for 15 min. The mixture was concentrated at 25° C. to remove most of the dioxane. The residue was poured into ice cold water to give a brown solid which was collected via filtration and dried with toluene (×2) azeotropically the give the title compound. LRMS m/z (M+1) Calcd: 351.1. Found 351.2

Workup

  1. concentrationThe mixture was concentrated at 25° C.
  2. customto remove most of the dioxane
  3. additionThe residue was poured into ice cold water
  4. customto give a brown solid which
  5. filtrationwas collected via filtration
  6. dry with materialdried with toluene (×2) azeotropically the

Sources & evidence

ORD record
ord-ec1679cbf7004edf89287e60c76b2a2d
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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