Hydrochloric Acid → 4-(1-Amino-ethyl)-benzoic acid methyl ester hydrochloride

HRID 1049092Notes

Reaction equation

HRID 1049092 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][CH:6]=1)[CH3:4].[ClH:15].O>CO.[Pd]>[ClH:15].[NH2:2][CH:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 73652604HCID 73652604, compound

Product 1

HCID 201342394-(1-Amino-ethyl)-benzoic acid methyl ester hydrochlorideYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of methyl 4-(1-(hydroxyimino)ethyl)benzoate (1.1 g, 5.6 mmol) and 12.0 M of hydrochloric acid in water (0.6 mL, 7.3 mmol) in methanol (50 mL) was added 10% palladium on carbon (0.20 g, 0.18 mmol). The reaction mixture was stirred overnight at room temperature. All insolubles were removed via filtration through celite and subsequent evaporation of the filtrate to dryness afforded the title compound as a white solid (1.12 g, 83%). LC-MS: (FA) ES+ 180; 1H NMR (400 MHz, MeO D) δ 8.09 (d, J=8.4 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 4.55 (q, J=6.8 Hz, 1H), 3.91 (s, 3H), 1.65 (d, J=6.9 Hz, 3H).

Workup

  1. customAll insolubles were removed via filtration through celite and subsequent evaporation of the filtrate to dryness

Sources & evidence

ORD record
ord-5695cf94a9694a15b3584d85e26b380c
Source dataset
uspto-grants-2016_07
Patent number
US09382197B2

Reaction notes

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