Diethyl Ether → 4-[[(Dimethylamino)methylene]amino]-3-pyridinol N,N-diethylcarbamate

HRID 362211Notes

Reaction equation

HRID 362211 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]([O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH2:13])=[O:5])[CH3:2].CCOCC>COC(OC)N(C)C>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4]([O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[N:13]=[CH:1][N:3]([CH3:14])[CH3:4])=[O:5])[CH3:15]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 543040194-Aminopyridin-3-yl diethylcarbamate

Product 1

HCID 677490664-[[(Dimethylamino)methylene]amino]-3-pyridinol N,N-diethylcarbamate

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

4-Amino-3-pyridinol N,N-diethylcarbamate (5.80 g) was refluxed for 30 minutes in 50 mL of N,N-dimethylformamide dimethyl acetal. At the end of this time the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (5% Et3N/ethyl acetate) to give, after concentration of the product-containing fractions, 4.63 g of chromatographically pure product. An analytically pure material was obtained by recrystallizatin from Et2O, m.p. 67°-69° C.

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (5% Et3N/ethyl acetate)
  3. customto give
  4. customAn analytically pure material was obtained

Sources & evidence

ORD record
ord-24b7764f3e5f4b73a225d5aa6c995454
Source dataset
uspto-grants-1999_02
Patent number
US05869480

Reaction notes

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