Formic Acid → HCID 11336764, compound

HRID 1351187Notes

Reaction equation

HRID 1351187 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:17]([NH2:19])=[C:16]([O:20][CH3:21])[C:15]([O:22][CH3:23])=[CH:14][C:13]=3[N:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH:26](O)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9]3[C:18]4[C:13]([N:12]=[CH:11][N:10]=3)=[CH:14][C:15]([O:22][CH3:23])=[C:16]([O:20][CH3:21])[C:17]=4[N:19]=[CH:26]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 21098409HCID 21098409, compound

Product 1

HCID 11336764HCID 11336764, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N4-(4-chloro-phenyl)-6,7-dimethoxy-quinazoline-4,5-diamine (160 mg, 0.48 mmol) (from Example 13, Step B, supra) in formic acid (2 mL) was heated at 110° C. for 2 hours. Aqueous NaOH solution was added to the reaction mixture to a pH 10–12. The solution was diluted with chloroform (100 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 3-(4-chloro-phenyl)-8,9-dimethoxy-3H-1,3,4,6-tetraaza-phenalene as an off white solid. (Yield 96 mg, 59%).

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-3740c370cd3e4f9a808c012f8f9b138a
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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