Sodium Bicarbonate → HCID 58266415, compound

HRID 1505936Notes

Reaction equation

HRID 1505936 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-5f3423383f6f4cb885a54179b484c11a
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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