Dimethyl acetylenedicarboxylate → HCID 178500758, compound

HRID 547377Notes

Reaction equation

HRID 547377 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[CH3:9][O:10][C:11]([C:13]#[C:14][C:15]([O:17][CH3:18])=[O:16])=[O:12]>C(Cl)(Cl)Cl>[O-:8][N+:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1]/[C:13](=[CH:14]\[C:15]([O:17][CH3:18])=[O:16])/[C:11]([O:10][CH3:9])=[O:12]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylate2×HCID 178507601HCID 178507601, compound

Product 1

HCID 178500758HCID 178500758, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2-aminopyridine-N-oxide in chloroform at 0° C. was added dropwise a solution of DMAD (1 eq.) in chloroform. After addition the cooling bath was removed and stirring was continued for 1 hour. A further 0.2 eq. of DMAD was added and stirring continued for 1 hour. The solution was filtered over a silica gel plug. After elution with EtOAc/PE (4:6), the product was eluted with MeOH/EtOAc. The combined MeOH/EtOAc-phases were concentrated to dryness. The title compound was obtained as a brown oil, which was used without further purification.

Workup

  1. additionAfter addition the cooling bath
  2. customwas removed
  3. stirringstirring
  4. waitcontinued for 1 hour
  5. filtrationThe solution was filtered over a silica gel plug
  6. washAfter elution with EtOAc/PE (4:6)
  7. washthe product was eluted with MeOH/EtOAc
  8. concentrationThe combined MeOH/EtOAc-phases were concentrated to dryness

Sources & evidence

ORD record
ord-40d387c9807545abb23b79ac3328350b
Source dataset
uspto-grants-2011_05
Patent number
US07939537B2

Reaction notes

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