Hydrochloric Acid → 2-Amino-1-(4-methoxyphenyl)propan-1-one--hydrogen chloride (1/1)

HRID 1699358Notes

Reaction equation

HRID 1699358 reaction equation
COC1C=CC(C(=O)C(Br)C)=CC=1.[N-]=[N+]=[N-].[Na+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:32])[CH:27]([N:29]=[N+]=[N-])[CH3:28])=[CH:22][CH:21]=1.[ClH:33]>C1COCC1.O.[Pd].CCOCC>[ClH:33].[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26](=[O:32])[CH:27]([NH2:29])[CH3:28])=[CH:24][CH:25]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 2991022-bromo-1-(4-methoxyphenyl)propan-1-oneHCID 15889767HCID 15889767, compound

Product 1

HCID 126265652-Amino-1-(4-methoxyphenyl)propan-1-one--hydrogen chloride (1/1)Yield 100%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

4′-Methoxy-2-bromopropiophenone (10 g, 41 mmol.) was dissolved in a mixture of THF (100 mL) and water (20 mL), followed by addition of sodium azide (6.5 g, 0.1 mole). The slurry was vigorously stirred for 5 hours and TLC indicated a completed conversion to 4′-methoxy-2-azidopropiophenone. The aqueous layer was then removed and the organic layer was further diluted with ethanol (200 mL). Concentrated hydrochloride (5 mL, about 60 mmol.) and palladium on carbon (10%, 2 g) were added and hydrogenation was performed using Parr apparatus at 20 psi for 1 hour. The product precipitated during the hydrogenation was re-dissolved by addition of methanol (100 mL). After filtration to remove the catalyst, the solution was concentrated to form a solid. It was stirred with ether (300 mL) and solids were filtered and dried under vacuum at 50° C. overnight to give the titled compound (8.8 g, 100%) MS: 180 (MH+), 162 (M-NH3). Proton NMR (DMSO-d6) δ: 7.96(2H, brs), 7.79(2H, d, J=8.4 Hz), 6.87(2H, d, J=8.4 Hz), 4.49(1H,brs), 1.17(2H, d, J=6.9 Hz).

Workup

  1. customThe aqueous layer was then removed
  2. additionthe organic layer was further diluted with ethanol (200 mL)
  3. customfor 1 hour
  4. customThe product precipitated during the hydrogenation
  5. dissolutionwas re-dissolved by addition of methanol (100 mL)
  6. filtrationAfter filtration
  7. customto remove the catalyst
  8. concentrationthe solution was concentrated
  9. customto form a solid
  10. filtrationwere filtered
  11. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-20c36959f4554abaabaf0c2543477ad8
Source dataset
uspto-grants-2002_02
Patent number
US06346534B1

Reaction notes

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