Fusaric Acid → 5-Butylpyridin-2-amine

HRID 1279571Notes

Reaction equation

HRID 1279571 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8](C(O)=O)=[N:9][CH:10]=1.C1(P([N:28]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>C(O)(C)(C)C>[NH2:28][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 3442Fusaric AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 184286505-Butylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Fusaric acid (2 g), diphenylphosphoryl azide (2.4 mL) and triethylamine (1.6 mL) in t-butanol (70 mL) were refluxed overnight. The contents were concentrated in vacuo and treated with 25% aqueous HBr (20 mL) for 24 hours. After neutralizing with 50% NaOH, contents were extracted with CH2Cl2, dried (MgSO4) and concentrated in vacuo to give 2-amino-5-(n-butyl)pyridine as an oil (1.1 g).

Workup

  1. concentrationThe contents were concentrated in vacuo
  2. additiontreated with 25% aqueous HBr (20 mL) for 24 hours
  3. extractionwere extracted with CH2Cl2
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76eea198a4c24ffc90a2dfde962ad0b0
Source dataset
uspto-grants-2002_09
Patent number
US06448286B1

Reaction notes

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