Pyridine → HCID 86745040, compound

HRID 486138

Reaction equation

HRID 486138 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=O)=[CH:5][CH:4]=1)=[O:2].Cl.[NH2:13][OH:14].N1C=CC=CC=1>C(O)C>[CH:1]([C:3]1[S:7][C:6]([C:8](=[N:13][OH:14])[O:10][CH3:11])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

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

Product 1

HCID 86745040HCID 86745040, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 5-formyl-2-thiophenecarboxylate, prepared according to Example 10, (6.26 g, 36.78 mmoles), hydroxylamine hydrochloride (3.07 g, 44.14 mmoles) and pyridine (3.49 g, 44.14 mmoles) in 200 ml of ethanol was refluxed for 2 hours. The ethanol was removed in vacuo, the residue dissolved in ether and washed with water. The organic layer was dried (magnesium sulfate) and evaporated to a yellow solid. Trituration with a small amount of ether furnished the title compound as a white solid (4.93 g, 72%), m.p. 164°-7° C. Oxime Z:E ratio:(82:18).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe ethanol was removed in vacuo
  3. dissolutionthe residue dissolved in ether
  4. washwashed with water
  5. dry with materialThe organic layer was dried (magnesium sulfate)
  6. customevaporated to a yellow solid

Sources & evidence

ORD record
ord-038889dfe10f49509407368a4d81b8a3
Source dataset
uspto-grants-1994_03
Patent number
US05290802

Linked notes

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