Hydrochloric Acid → HCID 19969410, compound

HRID 974783Notes

Reaction equation

HRID 974783 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH2:7][CH2:6]2.B(Br)(Br)Br.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl.C(OCC)(=O)C.O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH2:7][CH2:6]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 19969412HCID 19969412, compound

Product 1

HCID 19969410HCID 19969410, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 6-methoxy-2-(3-pyridyl)-1-tetralone (288 mg; 1.1 mmol) in CH2Cl2 (10 ml) was added, at 0° C. under argon, boron tribromide (215 μl; 2.2 mmol). It was left for 10 minutes and then, water, ethyl acetate and 2N NaHCO3 were added to bring the mixture to pH 9.5. The mixture was then acidified to pH 7-8 with 2N HCl and then extracted three times with ethyl acetate. The organic phase was washed with water and a saturated aqueous solution of NaCl , dried over MgSO4 filtered and evaporated. The residue was subjected to chromatography using a silica column, eluting with petroleum ether/ethyl acetate (1/9), to give 6-hydroxy-2-(3-pyridyl)-1-tetralone (208 mg; 79%) as a yellow solid.

Workup

  1. additionwas added, at 0° C. under argon
  2. extractionextracted three times with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materiala saturated aqueous solution of NaCl , dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. washeluting with petroleum ether/ethyl acetate (1/9)

Sources & evidence

ORD record
ord-72e00ef034f24c2ebefdfa61300e5b19
Source dataset
uspto-grants-1997_03
Patent number
US05607928

Reaction notes

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