Hydrochloric Acid → 1-Amino-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one hydrochloride

HRID 83863Notes

Reaction equation

HRID 83863 reaction equation
[N:1]([CH2:4][C:5](=[O:18])[C:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:16][CH3:17])[CH:10]=1)([CH3:8])[CH3:7])=[N+]=[N-].[ClH:19]>CO.[Pd]>[ClH:19].[NH2:1][CH2:4][C:5](=[O:18])[C:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([O:16][CH3:17])[CH:10]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86662246HCID 86662246, compound

Product 1

HCID 667407491-Amino-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one hydrochlorideYield 55.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A pressure bottle was charged with a solution of 1-azido-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one (99.5 g, 0.396 mol) in MeOH (1.0 L), 50% wet 10% Pd/C (25 g, 25% w/w.) and conc HCl (105 mL, 1.19 mol). The bottle was purged with hydrogen gas (40 psi×2), pressurized with hydrogen (45 psi) and agitated overnight. The reaction mixture was filtered through a Celite™ pad. The filtrate was evaporated to give a residue, which was triturated with Et2O to give 1-amino-3-(4-fluoro-3-methoxyphenyl)-3-methylbutan-2-one hydrochloride (57.4 g, 55%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.26 (b, 2H), 7.22 (m, 1H), 6.99 (dd, 1H), 6.89 (m, 1H), 3.87 (s, 3H), 3.81 (s, 2H), 1.50 (s, 6H).

Workup

  1. customThe bottle was purged with hydrogen gas (40 psi×2)
  2. filtrationThe reaction mixture was filtered through a Celite™ pad
  3. customThe filtrate was evaporated
  4. customto give a residue, which
  5. customwas triturated with Et2O

Sources & evidence

ORD record
ord-16712dcc9cb4432a8667267dd506660e
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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