Sodium Hydroxide → HCID 22036982, compound

HRID 1790000Notes

Reaction equation

HRID 1790000 reaction equation
P(Br)(Br)[Br:2].[CH3:5][C:6]1[CH:15]=[CH:14][C:13]2[CH2:12][CH2:11][CH2:10][CH:9](O)[C:8]=2[N:7]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:2][CH:9]1[C:8]2[N:7]=[C:6]([CH3:5])[CH:15]=[CH:14][C:13]=2[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 12307840HCID 12307840, compound2×

Product 1

HCID 22036982HCID 22036982, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus tribromide (0.0105 mol) was added dropwise at 0° C./5° C. under N2 flow to a mixture of (±)-5,6,7,8-tetrahydro-2-methyl-8-quinolinol (intermediate 17) (0.03 mol) in toluene (20 ml). The mixture was brought to room temperature and stirred at room temperature overnight. Ice water was added. The mixture was basified with a concentrated NaOH solution and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (6 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1; 20–45 μm). The pure fractions were collected and the solvent was evaporated, yielding 2 g (29%) of (±)-8-bromo-5,6,7,8-tetrahydro-2-methylquinoline (interm. 18).

Workup

  1. customwas brought to room temperature
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (6 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1; 20–45 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ec5c825169ea4d32846c8d18ec613a69
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

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