Hydrochloric Acid → HCID 69764691, compound

HRID 2414823Notes

Reaction equation

HRID 2414823 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:20]#N)=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:31].[K+].Cl.C(Cl)Cl.C[OH:38]>C(O)C1C=CC=CC=1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:20]([OH:38])=[O:31])=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21226129Dichloromethane methanolHCID 69763899HCID 69763899, compound

Product 1

HCID 69764691HCID 69764691, compound

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 7-cyano-1-(3,4-dichloro-benzyl)-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (3.60 g, 8.06 mmol) in benzyl alcohol (10 mL) is added KOH (3.00 g), and the reaction mixture is stirred at 160° C. for 0.5 h. The reaction mixture is allowed to cool to rt and is acidified with 2 M aqueous HCl. The reaction mixture is partitioned with EtOAc (3×20 mL). The combined organic phases are washed with brine, dried over MgSO4, filtered, and evaporated to yield a yellow oil. Chromatography over silica gel with CH2Cl2:MeOH 19:1 and then with MeOH provides the title compound as yellow solid.

Workup

  1. temperatureto cool to rt
  2. customThe reaction mixture is partitioned with EtOAc (3×20 mL)
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a yellow oil

Sources & evidence

ORD record
ord-79e2adb4ba0047dfbc8319a8c56531d8
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

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