Hydrochloric Acid → HCID 67396348, compound

HRID 1049095Notes

Reaction equation

HRID 1049095 reaction equation
O[N:2]=[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH3:15])[CH3:4].[ClH:16]>CO.[Pd]>[ClH:16].[NH2:2][CH:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH3:15])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 76779877HCID 76779877, compound

Product 1

HCID 67396348HCID 67396348, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of methyl 4-[N-hydroxyethanimidoyl]-3-methylbenzoate (0.348 g, 1.68 mmol) and 12.0 M aqueous hydrochloric acid (0.35 mL, 4.20 mmol) in methanol (15 mL) was added 10% palladium on carbon (0.11 g, 0.101 mmol). The reaction mixture was stirred under a balloon atmosphere of H2 overnight. All insolubles were then removed via filtration through celite and the filtrate was evaporated to dryness. The residue was redissolved in methanol/toluene and concentrated under reduced pressure to afford a white solid (0.385 g, 100%). LC-MS: (FA) ES+ 195; 1H NMR (300 MHz, DMSO) δ 7.15 (m Hz, 2H), 6.73 (d, J=8.1 Hz, 1H), 6.45-6.26 (m, 1H), 3.96 (dd, J=13.7, 6.9 Hz, 1H), 3.10 (s, 3H), 1.67 (s, 3H), 0.80 (d, J=6.8 Hz, 3H).

Workup

  1. customAll insolubles were then removed via filtration through celite
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was redissolved in methanol/toluene
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93f12ad85a314288a784ae27aa721de1
Source dataset
uspto-grants-2016_07
Patent number
US09382197B2

Reaction notes

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