Sodium Bicarbonate → HCID 58266415, compound

HRID 1888474Notes

Reaction equation

HRID 1888474 reaction equation
[CH2:1]([N:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:15][CH3:16])[CH:7]=[C:8]([O:13]C)[CH:9]=2)[CH2:4]1)[CH3:2].C(=O)([O-])O.[Na+]>Br>[CH2:1]([N:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:15][CH3:16])[CH:7]=[C:8]([OH:13])[CH:9]=2)[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58266768HCID 58266768, compound

Product 1

HCID 58266415HCID 58266415, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-ethyl-6,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline (280 mg, 1.27 mmol) in 48% aqueous hydrobromic acid (3 mL) was heated at 65° C. for 24 h. The mixture was added to saturated sodium hydrogen carbonate solution and extracted with ethyl acetate (3×50 mL). The combined organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The resultant solid was purified by flash chromatography (silica, 12 g column, ISCO, 0-20% (2N ammonia in MeOH) in DCM) to afford the title compound as an off white solid (153 mg, 58%). 1H NMR (CDCl3, 300 MHz): 6.11 (d, J=2.2 Hz, 1H), 5.93 (d, J=2.2 Hz, 1H), 3.67 (s, 3H), 3.55-3.49 (m, 2H), 2.72-2.58 (m, 6H), 1.21 (t, J=7.2 Hz, 3H). LCMS (Method B): RT=1.58 min, M+H+=208.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic phase was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resultant solid was purified by flash chromatography (silica, 12 g column, ISCO, 0-20% (2N ammonia in MeOH) in DCM)

Sources & evidence

ORD record
ord-956bfe0838164ba5a610cb386aa27cab
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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