Isobutyric Acid → 4-((2-Methylpropyl)amino)-3-pyridinol N,N-diethylcarbamate

HRID 361349Notes

Reaction equation

HRID 361349 reaction equation
[C:1](O)(=O)[CH:2]([CH3:4])[CH3:3].[BH4-].[Na+].[CH2:9]([N:11]([CH2:22][CH3:23])[C:12]([O:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[NH2:21])=[O:13])[CH3:10].[OH-].[Na+]>C1C=CC=CC=1>[CH2:22]([N:11]([CH2:9][CH3:10])[C:12]([O:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[NH:21][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:13])[CH3:23]

Participants

6

Reactant 4

HCID 6590Isobutyric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 543040194-Aminopyridin-3-yl diethylcarbamate

Product 1

HCID 542634884-((2-Methylpropyl)amino)-3-pyridinol N,N-diethylcarbamateYield 33%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of isobutyric acid (49.85 g) in 100 ml of benzene was treated with NaBH4 (6.91 g added portionwise). After the frothing subsided, 4-amino-3-pyridinol N,N-diethylcarbamate (4.90 g) was added and the mixture was heated at 85° C. for 3 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 2.05 g of solid. This product was recrystallized from hexane to give analytically pure material, m.p. 71°-75° 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-9306d75900894322aca538c4dd52edb5
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Reaction notes

Loading…