Ethanol → HCID 59396297, compound

HRID 2383054Notes

Reaction equation

HRID 2383054 reaction equation
[CH:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=C(C#N)[CH:15]=3)[CH2:10][CH2:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH2:19].[CH3:20][CH2:21][OH:22]>[OH-].[Na+]>[CH:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:20]([C:21]([OH:19])=[O:22])[CH:15]=3)[CH2:10][CH2:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 59396653HCID 59396653, compound

Product 1

HCID 59396297HCID 59396297, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

1-cyclohexyl-3,4-dihydroisoquinoline-7-carbonitrile (1.01 g) was dissolved in EtOH (15 mL), to which a 6 M aqueous NaOH solution (7.0 mL) was then added, followed by stirring under heating at reflux for 6 hours. Water was added to the mixture which was then washed with EtOAc. A 1 M aqueous HCl solution was added to the mixture to have a pH of about 3 and then a saturated aqueous sodium sulfate solution was added thereto. The mixture was extracted with a 4:1 mixed solution of chloroform-iPrOH, washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated to obtain 1-cyclohexyl-3,4-dihydroisoquinoline-7-carboxylic acid (1.09 g).

Workup

  1. additionwas then added
  2. temperatureunder heating
  3. temperatureat reflux for 6 hours
  4. washwas then washed with EtOAc
  5. additionA 1 M aqueous HCl solution was added to the mixture
  6. additiona saturated aqueous sodium sulfate solution was added
  7. extractionThe mixture was extracted with a 4:1 mixed solution of chloroform-iPrOH
  8. washwashed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5f2bdb9097ca4d3ebe607458b37022d3
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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