Propionic Acid → 4-Propylamino-3-pyridinol N,N-diethylcarbamate

HRID 361348Notes

Reaction equation

HRID 361348 reaction equation
[C:1](O)(=O)[CH2:2][CH3:3].[BH4-].[Na+].[CH2:8]([N:10]([CH2:21][CH3:22])[C:11]([O:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[NH2:20])=[O:12])[CH3:9].[OH-].[Na+]>C1C=CC=CC=1>[CH2:21]([N:10]([CH2:8][CH3:9])[C:11]([O:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[NH:20][CH2:1][CH2:2][CH3:3])=[O:12])[CH3:22]

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 543040194-Aminopyridin-3-yl diethylcarbamate

Product 1

HCID 543541644-Propylamino-3-pyridinol N,N-diethylcarbamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of propionic acid (58.5 ml) in 100 ml of benzene was treated with NaBH4 (9.6 g added portionwise). After the frothing subsided, 4-amino-3-pyridinol N,N-diethylcarbamate (5.30 g) was added and the mixture was heated at 80° C. for 2 hours. The reaction mixture was poured into a dilute NaOH solution and the aqueous phase was extracted with ethyl acetate (3×). The combined organics were washed with water and dried (saturated NaCl, MgSO4). The desired amine was purified via flash chromatography to give 3.2 g of solid, m.p. 60°-70° C. This product was combined with a crop obtained from another run and recrystallized from hexane to give analytically pure material, m.p. 75°-78° C.

Workup

  1. additionadded portionwise)
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×)
  3. washThe combined organics were washed with water
  4. dry with materialdried (saturated NaCl, MgSO4)
  5. customThe desired amine was purified via flash chromatography

Sources & evidence

ORD record
ord-02df8f0189cd4d19a518ccb816a7164c
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Reaction notes

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