Formic Acid → HCID 11208964, compound

HRID 1351171Notes

Reaction equation

HRID 1351171 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+].[CH:25](O)=O>C(Cl)(Cl)Cl>[CH3:14][O:13][C:12]1[CH:11]=[C:10]2[C:5]3[C:6]([N:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:25]=[N:22][C:4]=3[C:3]=1[O:2][CH3:1])=[N:7][CH:8]=[N:9]2

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 21098395HCID 21098395, compound

Product 1

HCID 11208964HCID 11208964, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 6,7-dimethoxy-N4-phenyl-quinazoline-4,5-diamine (80 mg, 0.27 mmol) (from Example 1, Step C, supra) in formic acid (5 mL) was heated at 110° C. for 2 hours. Aqueous NaOH solution was then 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 (1:0.04) as eluent to give the desired 8,9-dimethoxy-3-phenyl-3H-1,3,4,6-tetraaza-phenalene as a white solid. (Yield 45 mg, 54%).

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-65a1f602420d44f9b43dd12adc200368
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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