Sodium Hydroxide → HCID 73703363, compound

HRID 2307408Notes

Reaction equation

HRID 2307408 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([C:15](=O)[CH3:16])=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].Cl.[OH-:19].[NH4+:20].[OH-].[Na+]>C1COCC1>[OH:19][N:20]=[C:15]([C:9]1[CH:8]=[C:7]2[C:12]([CH2:13][CH2:14][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]2)=[CH:11][CH:10]=1)[CH3:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 13908798HCID 13908798, compoundHCID 20744333HCID 20744333, compound

Product 1

HCID 73703363HCID 73703363, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-acetyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid methyl ester, Preparation 8 (11.65 g, 50 mmol), ammonium hydroxide hydrochloride (7 g, 100 mmol) and sodium hydroxide (10N) (10 mL, 100 mmol) in THF (50 mL) was heated under reflux for 24 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo, and extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and the resultant filtrate was concentrated in vacuo. The residue obtained was purified by flash column chromatography on silica eluted with hexane/EtOAc (1:1) to provide the title compound as an oil (11.7 g, 94%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe resultant filtrate was concentrated in vacuo
  8. customThe residue obtained
  9. customwas purified by flash column chromatography on silica
  10. washeluted with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-18b1d4b6845142a0b3ebfe6725e8d730
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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