Sodium Hydroxide → HCID 11221316, compound

HRID 1351173Notes

Reaction equation

HRID 1351173 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[N:9]=[CH:8][N:7]=[C:6]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[C:4]=1[NH2:22].[OH-].[Na+].[C:25](OC(=O)CC)(=O)[CH2:26][CH3:27]>C(Cl)(Cl)Cl>[CH2:26]([C:27]1[N:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]2[C:5]3[C:10]([N:9]=[CH:8][N:7]=2)=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[C:4]=3[N:22]=1)[CH3:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31263Propionic anhydrideHCID 21098395HCID 21098395, compound

Product 1

HCID 11221316HCID 11221316, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 6,7-dimethoxy-N4-phenyl-quinazoline-4,5-diamine (130 mg, 0.44 mmol) (from Example 1, Step C, supra) in propionic anhydride (3 mL) (Aldrich) was heated at 170° C. for 2 hours. Aqueous NaOH solution was added to the reaction mixture to a pH 10–12. The solution was diluted with chloroform (50 mL). The organic layer was separated, dried over Na2SO4, and concentrated. This residue was purified by chromatography using EtOAc/Et3N (1:0.05) as eluent to give the desired 2-ethyl-8,9-dimethoxy-3-phenyl-3H-1,3,4,6-tetraaza-phenalene as an orange solid. (Yield 21 mg, 14%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThis residue was purified by chromatography

Sources & evidence

ORD record
ord-e8606e0c72f34aca815363eb9c6ff9ea
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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