Hydrochloric Acid → 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 32079Notes

Reaction equation

HRID 32079 reaction equation
[Br: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.Cl.[OH-].[Na+]>C1COCC1>[Br: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 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 734461306-bromo-3,4-dihydro-1H-naphthalen-2-one Oxime

Product 1

HCID 100595666-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of BH3-THF complex (1M) (35.9 mL, 35.9 mmol) was added drop-wise to a stirred solution of 6-bromo-3,4-dihydro-1H-naphthalen-2-one oxime (Step A) (3.450 g, 14.37 mmol) in THF (125 ml) at 0° C. The mixture was warmed to RT and to reflux for 24 h. The reaction was cooled to RT and 1 N aqueous HCl was added carefully until the mixture was acidic and the system was stirred until no further gas was evolved. The solution was made basic by the addition of NaOH and the aqueous layer was extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated in vacuo to afford the crude title compound, which was purified by flash column chromatography to yield the title compound. MS (APCI pos) 228 (M+H).

Workup

  1. temperatureto reflux for 24 h
  2. temperatureThe reaction was cooled to RT
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto afford the crude title compound, which
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-3c302a1131744702a5086e89cb68d9fa
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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