3-Buten-1-amine → HCID 68538578, compound

HRID 1432111Notes

Reaction equation

HRID 1432111 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[N:10]=1)[C:5]([OH:7])=[O:6].[CH2:13]([NH2:17])[CH2:14][CH:15]=[CH2:16]>O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[O-]S([O-])(=O)=O.[Cu+2]>[CH2:13]([NH:17][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[N:10]=1)[C:5]([OH:7])=[O:6])[CH2:14][CH:15]=[CH2:16]

Participants

6

Reactant 2

HCID 4437323-Buten-1-amineHCID 27821242-Chloro-6-methoxypyridine-4-carboxylic acid

Product 1

HCID 68538578HCID 68538578, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 311Citric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1.0 g (5.3 mmol) 2-chloro-6-methoxy-isonicotinic acid, 4.4 g (53 mmol, 86% pure by NMR) but-3-enylamine and 85 mg (0.53 mmol) CuSO4 in 10 ml H2O is stirred in a pressurized reaction vessel for 36 h at 140° C. The reaction mixture is diluted with an 0.5 M aqueous citric acid and extracted two times with EtOAc. The combined extracts are washed with citric acid solution, water and brine, dried over Na2SO4, filtered and the solvent is evaporated. Chromatography on silica gel yields the title compound as an off-white powder.

Workup

  1. extractionextracted two times with EtOAc
  2. washThe combined extracts are washed with citric acid solution, water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-146ff95ceabd4ed0a84a666f54773b9d
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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