Sulfuric Acid → 7-Chloroisoquinoline-3-carbaldehyde

HRID 1432889Notes

Reaction equation

HRID 1432889 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][NH:13][C:12]([CH2:19]Br)(CBr)[CH:11]=2.[OH-:21].[Na+]>O>[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([CH:19]=[O:21])[N:13]=[CH:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 867609777-Chloro-3,3-dibromomethylisoquinoline

Product 1

HCID 541450337-Chloroisoquinoline-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A 20 mL of 80% H2SO4 is added 7-chloro-3,3-dibromomethyl isoquinoline (0.69 g, 2.06 mmol) is heated to 150° C. for 16 hours. The solution is then cooled to ambient temperatures and diluted with 40 mL of H2O. The resulting solution is basified to pH=11 with 1N NaOH. The aqueous solution is extracted with CH2Cl2. The organic solution is washed with H2O and a saturated NaCl solution. The organic layer is dried over MgSO4, filtered and concentrated to give the product as an oil (0.25 g, 1.3 mmol). 1H NMR (CDCl3, 300 MHz) δ10.0 (s, 1H), 9.30 (s, 1H), 8.36 (s, 1H), 8.07 (s, 1H), 7.95 (d, 1H), 7.78 (d, 1H). MS (EI): m/z 191, 193 (M+), Cl pattern.

Workup

  1. temperatureThe solution is then cooled to ambient temperatures
  2. extractionThe aqueous solution is extracted with CH2Cl2
  3. washThe organic solution is washed with H2O
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b68a3482d84d494db4976b5cc81f4654
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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