Sodium Hydroxide → HCID 58246369, compound

HRID 242101Notes

Reaction equation

HRID 242101 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22]C)[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>Br>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58246321HCID 58246321, compound

Product 1

HCID 58246369HCID 58246369, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1-[1-(6-Chloropyridin-2-yl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline (550 mg, 1.68 mmol) in 48% aqueous hydrobromic acid (3.8 ml) was heated under reflux for 4 hours. After cooling to room temperature the reaction mixture was poured on ice water. 10% aqueous sodium hydroxide solution was added until pH 8 was reached. The mixture was extracted with dichloromethane (3×). The combined organic extracts were dried (MgSO4), concentrated in vacuo and purified by flash chromatography (silica, dichloromethane, methanol). Yield: 220 mg (0.70 mmol, 42%).

Workup

  1. temperatureunder reflux for 4 hours
  2. additionwas poured on ice water
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (silica, dichloromethane, methanol)

Sources & evidence

ORD record
ord-3a62633a04b64ff7a5a17c40d364d5af
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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