Sodium Sulfate → N-methyl-4-o-tolylpyridin-3-amine

HRID 877957Notes

Reaction equation

HRID 877957 reaction equation
[C:1]([NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])(OC(C)(C)C)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 70663189N-Boc-4-o-tolyl-pyridin-3-ylamine

Product 1

HCID 18403336N-methyl-4-o-tolylpyridin-3-amineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-Boc-4-o-tolyl-pyridin-3-ylamine (45 mg, 0.158 mmol) in THF (0.5 mL) under argon was treated with LAH in THF (1.0M, 0.20 mL, 0.2 mmol). The reaction mixture was then heated to reflux for 6 hours. After cooling, Na2SO4×10H2O was carefully added and the reaction mixture was stirred for 1 h after which a colorless solid formed. The solid was removed by filtration and all volatiles were evaporated to yield the desired compound as a solid (29 mg, 93%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 6 hours
  3. temperatureAfter cooling
  4. customformed
  5. customThe solid was removed by filtration
  6. customall volatiles were evaporated

Sources & evidence

ORD record
ord-b60b258825d5475a840662c4ad9b07af
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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