Hydrochloric Acid → HCID 178515328, compound

HRID 538061Notes

Reaction equation

HRID 538061 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[C:21](=[O:22])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:23])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl>CO>[O:23]=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][C:21](=[O:22])[N:12]1[CH2:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178501106HCID 178501106, compound

Product 1

HCID 178515328HCID 178515328, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

trans-4-(1,3-Dioxo-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-cyclo hexanecarboxylic acid methyl ester (2.2 g, 6.98 mmol) was dissolved in 20 mL of methanol, 5 mL of 15% NaOH solution were added and the mixture heated at 40° C. for 4 hours. The reaction was allowed to cool down to room temperature and the mixture neutralized with 2N HCl solution and extracted with DCM. The organic phase was dried over Na2SO4 and the solvent removed under reduced pressure. The residue was crystallized from a mixture of acetone-H2O (1:1), affording 700 mg of the desired product (33% yield).

Workup

  1. temperatureto cool down to room temperature
  2. extractionextracted with DCM
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent removed under reduced pressure
  5. customThe residue was crystallized from a mixture of acetone-H2O (1:1)

Sources & evidence

ORD record
ord-469ac773f5874f4eaea219c9224aa6dc
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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