Methanol → 2-Amino-N-(5-methyl-2-pyridinyl)benzamide

HRID 269725Notes

Reaction equation

HRID 269725 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)=[N:6][CH:7]=1.CO.[BH4-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 840320N-(5-methylpyridin-2-yl)-2-nitrobenzamideHCID 4311764Sodium borohydride

Product 1

HCID 113791632-Amino-N-(5-methyl-2-pyridinyl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of N-(5-methylpyridin-2-yl)-2-nitrobenzamide (1.5 g, 5.8 mmol) and Ni(OAC)2.4H2O (2.9 g, 11.7 mmol) in THF (20 mL) and methanol (40 mL) at 0° C. was added, in small portions, sodium borohydride (0.88 g, 23.2 mmol). After complete addition and an additional 5 min, the solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate (200 mL) and 50% conc NH4OH (200 mL). The organic phase was separated and washed again with 50% conc NH4OH, followed by brine, then dried with MgSO4, filtered and concentrated in vacuo to give 1.25 g (95%) of a light yellow solid.

Workup

  1. additionAfter complete addition
  2. customan additional 5 min, the solvent was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate (200 mL) and 50% conc NH4OH (200 mL)
  4. customThe organic phase was separated
  5. washwashed again with 50% conc NH4OH
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45e9686a6bc046049c1c53ba3e3341f7
Source dataset
uspto-grants-2008_11
Patent number
US07449457B2

Reaction notes

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