n-(5-Bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide → (2-Amino-3,4,5-trimethoxyphenyl)-n-(5 bromo(2-pyridyl))carboxamide

HRID 12157Notes

Reaction equation

HRID 12157 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[C:12]=2[N+:23]([O-])=O)=[O:10])=[N:6][CH:7]=1>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:23][C:12]1[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=1[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:10]

Participants

4

Reactant 1

HCID 22596319n-(5-Bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide

Product 1

HCID 85783824(2-Amino-3,4,5-trimethoxyphenyl)-n-(5 bromo(2-pyridyl))carboxamideYield 77.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of N-(5-bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide (790 mg, 1.92 mmol) in ethyl acetate (5 ml) was added tin chloride (II) hydrate (1.73 g, 7.67 mmol). The mixture was stirred under reflux condition for 2 hrs. After filtered by Celite, the filtrate was added 1N sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to give (2-amino-3,4,5-trimethoxyphenyl)-N-(5-bromo(2-pyridyl))carboxamide (570 mg, 77%). MS found for C15H16BrN3O4 M+=382, (M+2)+=384.

Workup

  1. temperatureunder reflux condition for 2 hrs
  2. filtrationAfter filtered by Celite
  3. additionthe filtrate was added 1N sodium hydroxide solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6ff2f43c9804f5a977194ab3f2eb2d2
Source dataset
uspto-grants-2010_06
Patent number
US07727981B2

Reaction notes

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