Hydrochloric Acid → 6-Fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochloride

HRID 1592335Notes

Reaction equation

HRID 1592335 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=[N:12]O)[CH2:6][CH2:5]2.[ClH:14]>[Pd].CO>[ClH:14].[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH2:12])[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 860515846-fluoro-3,4-dihydronaphthalen-2(1H)-one Oxime

Product 1

HCID 196993636-Fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine hydrochlorideYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-fluoro-3,4-dihydronaphthalen-2(1H)-one oxime (1.58 g, 8.81 mmol), methanol (25 mL), conentrated hydrochloric acid (2 mL) and 10% palladium on charcoal (316 mg) was shaken in a pressure bottle under a hydrogen atmosphere (55 psig). After 18 hours, the mixture was filtered and the solid washed with methanol. The filtrate was concentrated under vacuum, and the residue was washed with ether, dried by concentration from benzene, and dried further under vacuum to provide a white solid (1.48 g, 83%).

Workup

  1. filtrationthe mixture was filtered
  2. washthe solid washed with methanol
  3. concentrationThe filtrate was concentrated under vacuum
  4. washthe residue was washed with ether
  5. dry with materialdried by concentration from benzene
  6. customdried further under vacuum

Sources & evidence

ORD record
ord-585afe5e44ee4a9c8b76bd8f4bd5ae18
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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