Hydrochloric Acid → HCID 67395898, compound

HRID 1037955Notes

Reaction equation

HRID 1037955 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-8d4676bbc83a4344ab02ddb529e5be46
Source dataset
uspto-grants-2013_10
Patent number
US08546588B2

Reaction notes

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