Sulfuric Acid → HCID 59396328, compound

HRID 2383030Notes

Reaction equation

HRID 2383030 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]3C(=O)C(=O)O[C:9]32[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O>CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]=[C:9]2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59396224HCID 59396224, compound

Product 1

HCID 59396328HCID 59396328, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

9-chloro-10b-cyclohexyl-6,10b-dihydro-5H-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione (2.37 g) was dissolved in MeOH (16 mL), and a solution of sulfuric acid (8 mL) in MeOH (24 mL) was added thereto, followed by stirring under heating at reflux for 18 hours. The reaction mixture was left to cool and then the solvent was evaporated. The reaction mixture was neutralized by an aqueous 1 M sodium hydroxide solution, extracted with chloroform, washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and then the resulting residue was dried to obtain 7-chloro-1-cyclohexyl-3,4-dihydroisoquinoline (1.78 g).

Workup

  1. temperatureunder heating
  2. temperatureat reflux for 18 hours
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. customthe solvent was evaporated
  6. extractionextracted with chloroform
  7. washwashed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe resulting residue was dried

Sources & evidence

ORD record
ord-664262fa30aa40b0a7ac63719efcea59
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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