Ammonium Acetate → (2-Methoxypyridin-3-yl)methanamine

HRID 1363128Notes

Reaction equation

HRID 1363128 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=O)=[CH:7][CH:6]=[CH:5][N:4]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:17].[Na+]>>[NH2:17][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 125333912-Methoxypyridine-3-carbaldehyde

Product 1

HCID 16793564(2-Methoxypyridin-3-yl)methanamineYield 69.9%

Procedure

A round bottom flask was charged with 0.44 g (3.23 mM) of 2-methoxy-3-pyridine carboxaldehyde (24), 1.24 g (16.15 mM) of ammonium acetate, and 0.61 g (19.69 mM) of sodium cyanoborohydride. The flask was then flushed with argon, and then 50 mL of dry MeOH was added by syringe. The reaction was stirred for 2 days, at which point the MeOH was evaporated off 25 mL of water was added, and the mixture was brought to pH 2 with conc. HCl. This was extracted twice with EtOAc to remove the alcohol side product. The mixture was brought to pH 10 using sodium hydroxide pellets, saturated with NaCl, and extracted twice with DCM and once with EtOAc. The combined organics were dried and evaporated to give 0.31 g (69%) of 3-aminomethyl-2-methoxypyridine (25).

Workup

  1. customThe flask was then flushed with argon
  2. addition50 mL of dry MeOH was added by syringe
  3. customwas evaporated off 25 mL of water
  4. additionwas added
  5. extractionThis was extracted twice with EtOAc
  6. customto remove the alcohol side product
  7. extractionsaturated with NaCl, and extracted twice with DCM and once with EtOAc
  8. customThe combined organics were dried
  9. customevaporated

Sources & evidence

ORD record
ord-622e4114370142a98883baafc3dbe339
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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