Hydroxyamine hydrochloride → 8-[(E)-(hydroxyimino)methyl]-5-indolizinecarboxylic acid ethyl ester

HRID 1037081Notes

Reaction equation

HRID 1037081 reaction equation
[CH:1]([C:3]1[C:11]2[N:7]([CH:8]=[CH:9][CH:10]=2)[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1)=O.[NH2:17][OH:18].Cl.CC([O-])=O.[Na+]>C1COCC1.O>[OH:18]/[N:17]=[CH:1]/[C:3]1[C:11]2[N:7]([CH:8]=[CH:9][CH:10]=2)[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86685519Ethyl 8-formylindolizine-5-carboxylate

Product 1

HCID 895779068-[(E)-(hydroxyimino)methyl]-5-indolizinecarboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 8-formylindolizine-5-carboxylate (100 mg, 0.46 mmol) and NH2OH.HCl (48 mg, 0.69 mmol) in THF (10 mL) and H2O (3 mL) at rt was added NaOAc (75 mg, 0.92 mmol). The reaction mixture was stirred at rt for 2 h. The mixture was extracted with EA (2×20 mL). The organic layers was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was used in next step without further purification.

Workup

  1. extractionThe mixture was extracted with EA (2×20 mL)
  2. dry with materialThe organic layers was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was used in next step without further purification

Sources & evidence

ORD record
ord-ce59cd90490940ac835d2a8662710052
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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