Hydrochloric Acid → HCID 67395898, compound

HRID 588495Notes

Reaction equation

HRID 588495 reaction equation
O/[N:2]=[C:3](/[C:5]1[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=1)\[CH3:4].[ClH:14]>CO.[OH-].[OH-].[Pd+2]>[ClH:14].[NH2:2][CH:3]([C:5]1[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=1)[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58418290HCID 58418290, compound

Product 1

HCID 67395898HCID 67395898, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of methyl 5-[(1E)-N-hydroxyethanimidoyl]thiophene-2-carboxylate (3.43 mg, 17.2 mmol) and hydrochloric acid (12.0 M, 1.8 mL, 22.4 mmol) in methanol (100 mL) was added Pearlman's catalyst (84.6 mg, 0.2 mmol). The resulting reaction mixture was shaken under a 60 psi atmosphere of H2 for 4 days. The catalyst was removed by filtration through celite and the solvent was removed to afford a white solid (3.55 g, 93%). LC-MS: (FA) ES+ 186)

Workup

  1. customThe resulting reaction mixture
  2. customThe catalyst was removed by filtration through celite
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-f061ace867e340d4b4c6f418510310b9
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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