Water → HCID 10496423, compound

HRID 1604569Notes

Reaction equation

HRID 1604569 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26].O>ClCCl>[Br:21][CH2:22][CH2:23][CH2:24][C:25]([NH:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1)=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 702254-Bromobutyryl chlorideHCID 10749820HCID 10749820, compound

Product 1

HCID 10496423HCID 10496423, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl (E)-3-(6-aminopyridin-3-yl)acrylate (700 mg) and triethylamine (477 mg) in dichloromethane (6 ml) was added dropwise 4-bromobutyryl chloride (801 mg) under nitrigen in ice water bath and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water, saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and evaporated in vacuo. the residue was chromatographed on silica gel eluting with chloroform and purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:1, v/v) to give methyl (E)-3-[6-(4-bromobutyramido)pyridin-3-yl]acrylate (101 mg).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water, saturated sodium bicarbonate aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customthe residue was chromatographed on silica gel eluting with chloroform
  6. custompurified by preparative thin-layer chromatography (n-hexane

Sources & evidence

ORD record
ord-f53457a320494d08a5a732a2eabb625f
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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