Hydroxyamine hydrochloride → Ethyl 4-cyano-5-methyl-1H-pyrrole-2-carboxylate

HRID 2233816Notes

Reaction equation

HRID 2233816 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][C:7]=1[CH3:8])=O.Cl.[NH2:15]O>CCO.CN(C=O)C.O=S(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][C:7]=1[CH3:8])#[N:15]

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 809639ethyl 4-formyl-5-methyl-1H-pyrrole-2-carboxylate2×

Product 1

HCID 58066127Ethyl 4-cyano-5-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Ethyl 4-formyl-5-methyl-1H-pyrrole-2-carboxylate (Intermediate 15, 0.2 g, 1.1 mmol) and hydroxylamine hydrochloride (0.08 g, 1.1 mmol) were dissolved in EtOH (10 ml) and refluxed for 1.5 hours. The mixture was concentrated under vacuum to give yellow solid, which was dissolved in DMF (5 ml) before addition of SOCl2 (0.35 ml) at 0° C. The solvent was removed under vacuum after the completion of the reaction and the residue was partitioned between water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc twice. The combined organic extracts were dried over MgSO4 and concentrated to give brown solid (0.16 g, crude).

Workup

  1. temperaturerefluxed for 1.5 hours
  2. concentrationThe mixture was concentrated under vacuum
  3. customto give yellow solid, which
  4. customThe solvent was removed under vacuum
  5. customafter the completion of the reaction
  6. customthe residue was partitioned between water and EtOAc
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with EtOAc twice
  9. dry with materialThe combined organic extracts were dried over MgSO4
  10. concentrationconcentrated
  11. customto give brown solid (0.16 g, crude)

Sources & evidence

ORD record
ord-2d22b804e9bb4625b9d86bc41da880d4
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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