Acetic Acid → N-Butyl-3-pyridinamine

HRID 496780Notes

Reaction equation

HRID 496780 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:8](=O)[CH2:9][CH2:10][CH3:11].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:8]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 261ButanalHCID 100093-AminopyridineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22322612N-Butyl-3-pyridinamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 941 mg (10 mmol) of 3-aminopyridine and 0.9 mL of butyraldehyde in 30 mL of CH3OH was added 10 mL of glacial acetic acid. The mixture was stirred at room temperature for 1 hour, then the reaction was cooled with an ice bath, and 650 mg (10.3 mmol) of sodium cyanoborohydride was added.

Workup

  1. temperaturethe reaction was cooled with an ice bath

Sources & evidence

ORD record
ord-731bff6af07a4fb0b2f554336eb26ace
Source dataset
uspto-grants-2005_09
Patent number
US06946481B1

Reaction notes

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