Carbon Dioxide → 1-Butylisoquinoline-7-carboxylic acid

HRID 349056

Reaction equation

HRID 349056 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.C([Li])(CC)C.[C:21](=[O:23])=[O:22]>C(OCC)C>[CH2:12]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:21]([OH:23])=[O:22])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 210859957-Bromo-1-butylisoquinolineHCID 178418400CID 53628100

Product 1

HCID 210851771-Butylisoquinoline-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a −60° C. solution of 7-bromo-1-butylisoquinoline prepared in step 1 (940 mg, 3.55 mmol) in diethyl ether (15 mL) was added sec-butyl lithium (3.0 mL, 1.3 M cyclohexanes, 3.90 mmol) to yield a dark green solution. The reaction mixture was stirred at −60° C. for an additional 15 minutes at which time carbon dioxide gas was bubbled through the solution for 20 minutes with the aid of a gas dispersion tube. The resulting solution was then allowed to warm to room temperature and concentrated under reduced pressure to yield a pink solid. The residue was partitioned between ethyl acetate and water and then acidified to pH 7 with 1 N hydrochloric acid. The aqueous phase was extracted again with ethyl acetate and the combined organic phases were washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated to yield 1-butylisoquinoline-7-carboxylic acid (299 mg). ESI MS m/z 230 [M+H]+.

Workup

  1. customto yield a dark green solution
  2. customwas bubbled through the solution for 20 minutes with the aid of a gas dispersion tube
  3. concentrationconcentrated under reduced pressure
  4. customto yield a pink solid
  5. customThe residue was partitioned between ethyl acetate and water
  6. extractionThe aqueous phase was extracted again with ethyl acetate
  7. washthe combined organic phases were washed with saturated sodium chloride
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-885ba77874264456a2ada432f92109f6
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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