N-Methylbutylamine → 4-[[(N-methyl-N-butylamino)methylene]amino]-3-pyridinol

HRID 399388

Reaction equation

HRID 399388 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH3:3].CN[CH2:15][CH2:16][CH2:17]C.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>C1(C)C=CC=CC=1>[CH3:3][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH2:1][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 8068N-MethylbutylamineHCID 6097028Ammonium SulfateHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

Product 1

HCID 153809364-[[(N-methyl-N-butylamino)methylene]amino]-3-pyridinolYield 64.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[[(dimethylamino)methylene]amino]-3-pyridinol (7.50 g), N-methylbutylamine (8.10 g), ammonium sulfate (0.600 g), and anhydrous toluene (25 mL) was heated at reflux under nitrogen for 2.25 hours. The solution was concentrated under reduced pressure and the crude product chromatographed on silica gel (10% methanol in dichloromethane) to afford 6.04 g of solid. Recrystallization from ethyl acetate/hexanes afforded 3.90 g of a crystalline material, m.p. 83°-85° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 2.25 hours
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe crude product chromatographed on silica gel (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f92cdec8dc224a42b345b4178a8b31c1
Source dataset
uspto-grants-1998_10
Patent number
US05821239

Linked notes

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