Bromine → HCID 69905451, compound

HRID 427337Notes

Reaction equation

HRID 427337 reaction equation
[ClH:1].[NH2:2][C@@H:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:13][CH3:14])[CH2:4]1.C([O-])(=O)C.[Na+].[Br:20]Br>C(O)(=O)C>[ClH:1].[NH2:2][C@@H:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([Br:20])[CH:7]=[CH:8][C:9]=2[O:13][CH3:14])[CH2:4]1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 12280574HCID 12280574, compound

Product 1

HCID 69905451HCID 69905451, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(R)-2-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalene hydrochloride (5.0 g, 23 mmol) was dissolved in acetic acid (300 mL) under nitrogen atmosphere. Sodium acetate (5.5 g, 70 mmol) was added and bromine (3.5 g, 23 mmol) was then added in one portion. The mixture was stirred for 5 minutes at room temperature. The solvent was removed in vacuo to give a solid residue which was partitioned between ethyl acetate and NaOH (2 M). The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined and dried (Na2SO4). The solvent was removed in vacuo to give a brown oily residue. The HCl salt was precipitated from diethyl ether/methylene chloride by the addition of HCl in diethyl ether (3 M): yield 7.7 g (94%). Recrystallization from methanol gave the title compound as needle crystals: mp 264-265° C.; [α]21D+54° (c 1, MeOH); EIMS (70 eV) m/z (relative intensity) 257 (30, M+, 81Br), 255 (31, M+, 79Br).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a solid residue which
  3. customwas partitioned between ethyl acetate and NaOH (2 M)
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed in vacuo
  8. customto give a brown oily residue
  9. customThe HCl salt was precipitated from diethyl ether/methylene chloride by the addition of HCl in diethyl ether (3 M)
  10. customRecrystallization from methanol

Sources & evidence

ORD record
ord-3766eeb7fd5645db9a3f3ff597a8e319
Source dataset
uspto-grants-2001_11
Patent number
US06313118B1

Reaction notes

Loading…