Hydroxyamine hydrochloride → HCID 53801930, compound

HRID 399810Notes

Reaction equation

HRID 399810 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:4]=1)=O.Cl.[NH2:19][OH:20].C[O-].[Na+]>CO>[OH:20][N:19]=[CH:1][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 18945251HCID 18945251, compound

Product 1

HCID 53801930HCID 53801930, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(3-formylpyrrol-1-yl)benzoate (10.2 g) was added to a mixture of hydroxylamine hydrochloride (3.1 g) and 28% methanolic sodium methoxide (8.6 ml) in methanol (100 ml) and the whole was stirred for 3 hours at ambient temperature. The solvent was removed by concentration. To the residue was added a mixture of ethyl acetate, tetrahydrofuran and water, and the mixture was adjusted to pH 2 with 6N-hydrochloric acid. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give methyl 3-[3-(hydroxyiminomethyl)pyrrol-1-yl]benzoate (9.24 g) (oil).

Workup

  1. customThe solvent was removed by concentration
  2. additionTo the residue was added
  3. additiona mixture of ethyl acetate, tetrahydrofuran and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d18801a503264fdfad0c7da39148ed61
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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