Benzaldehyde → 4-Benzylamino-3-pyridinol N,N-diethylcarbamate

HRID 361347Notes

Reaction equation

HRID 361347 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].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC.[BH4-].[Na+]>C1C=CC=CC=1.CO.C(OCC)(=O)C.O>[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[NH:13][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:5])[CH3:15]

Participants

9

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 543040194-Aminopyridin-3-yl diethylcarbamate

Product 1

HCID 538900954-Benzylamino-3-pyridinol N,N-diethylcarbamate

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-3-pyridinol N,N-diethylcarbamate (2.09 g) was refluxed overnight in 100 mL of benzene containing benzaldehyde (1.50 g) and Et3N (2.0 g). At the end of this time the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography to give, after concentration of the product-containing fractions, 1.91 g of chromatographically pure product. This was combined with the product of another run (total 4.20 g) and dissolved in MeOH (50 mL). NaBH4 (0.37 g) was added in portions and after 30 minutes the reaction mixture was distributed between water and ethyl acetate. The organic phase was dried, concentrated and purified by flash chromatography. The product-containing fractions were concentrated and the residue was recrystallized from ethyl acetate to give 1.85 g of analytically pure product, m.p. 71°-73° 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
  3. customto give
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. custompurified by flash chromatography
  7. concentrationThe product-containing fractions were concentrated
  8. customthe residue was recrystallized from ethyl acetate
  9. customto give 1.85 g of analytically pure product, m.p. 71°-73° C.

Sources & evidence

ORD record
ord-9770bf40ba8948f796731d3027739607
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Reaction notes

Loading…