Pyridine → HCID 72740488, compound

HRID 1397238

Reaction equation

HRID 1397238 reaction equation
Cl.[NH2:2][OH:3].N1C=CC=CC=1.[CH:10]([C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=1)=O>CCO>[OH:3][N:2]=[CH:10][C:12]1[S:16][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 818924Methyl 5-formylthiophene-2-carboxylate

Product 1

HCID 72740488HCID 72740488, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (420 mg, 6.1 mmol) and pyridine (0.5 mL) were added to a solution of methyl 5-formylthiophene-2-carboxylate (690 mg, 4.1 mmol) in EtOH (25 mL). The reaction mixture was refluxed for 3 h, cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in diethyl ether, the organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get product methyl 5-((hydroxyimino)methyl)thiophene-2-carboxylate (440 mg, yield 60%), which was carried through without any further purification. 1H NMR (400 MHz, DMSO-d6) δ 12.5 (s, 1H), 7.98 (s, 1H), 7.78 (d, J=4.1 Hz, 1H), 7.51 (d, J=4.1 Hz, 1H), 3.82 (s, 3H). MS (ESI) m/z: Calculated for C7H7NO3S: 185.01. found: 186.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-431d63bfd1244dc285cf1cc976b2662e
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Linked notes

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