Hydrochloric Acid → HCID 67254187, compound

HRID 1049098Notes

Reaction equation

HRID 1049098 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[O:15][CH3:16])[CH3:4].[ClH:17]>CO.[Pd]>[ClH:17].[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[O:15][CH3:16])[CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 76779960HCID 76779960, compound

Product 1

HCID 67254187HCID 67254187, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of methyl 4-(1-(hydroxyimino)ethyl)-3-methoxybenzoate (0.417 g, 1.87 mmol) in methanol (17 mL) was added 12.0 M aqueous hydrochloric acid (0.389 mL, 4.67 mmol) and 10% palladium on carbon (0.120 g, 0.113 mmol). The reaction mixture was stirred under a balloon atmosphere of H2 overnight. The catalyst was removed via filtration through celite and evaporation of the filtrate to dryness afforded the title compound (0.471 g, 100%). LC-MS: (FA) ES+ 209; 1H NMR (300 MHz, DMSO) δ 8.20 (s, 3H), 7.64 (m, 1H), 7.55 (s, 2H), 4.60 (m, 1H), 3.91 (s, 3H), 3.86 (s, 3H), 1.46 (d, J=6.9 Hz, 3H).

Workup

  1. customThe catalyst was removed via filtration through celite and evaporation of the filtrate to dryness

Sources & evidence

ORD record
ord-126e7135bf804c1ab340ede8adcaf6cb
Source dataset
uspto-grants-2016_07
Patent number
US09382197B2

Reaction notes

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