Ethyl Acetate → HCID 86753232, compound

HRID 399842Notes

Reaction equation

HRID 399842 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.Cl.[NH2:19][OH:20].C[O-].[Na+].C(OCC)(=O)C>CO.O>[OH:20][N:19]=[CH:1][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 18945307Methyl 3-formyl-5-(1H-pyrrol-1-yl)benzoate

Product 1

HCID 86753232HCID 86753232, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 3-formyl-5-(pyrrol-1-yl)benzoate (2.0 g) was added to a mixture of hydroxylamine hydrochloride (0.61 g) and 28% methanolic sodium methoxide (1.8 ml) in methanol (20 ml) and the whole was stirred for 22 hours at ambient temperature. The reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was successively washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and ethyl acetate (20:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-hydroxyiminomethyl-5-(pyrrol-1-yl)benzoate (1.69 g).

Workup

  1. washThe organic layer was successively washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and ethyl acetate (20:1)
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-3834160d55fc4437b23fd4d324ba60ab
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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