Hydrochloric Acid → 2-Benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 617779Notes

Reaction equation

HRID 617779 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([OH:14])=[O:13])[NH:3]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>[OH-].[Na+]>[C:15]([N:3]1[CH:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 27241351,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Product 1

HCID 5700052-Benzoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

This compound was prepared according to Hein et. al., J. Amer. Chem. Soc.; 1962, 84, 4487-4494, incorporated by reference herein in its entirety. Thus, a slurry of 1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrochloride (20.3 g, 95 mmol) in 2N NaOH (150 ml) was treated with benzoyl chloride (13.4 ml, 114 mmol) dropwise over 30 minutes. The mixture was stirred a further 1.5 hours, acidified to pH 2-3 (4N HCl), and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to afford 16.4 g (61) of the title compound following recrystallization (acetone/water); MS: 280 m/z (M-H)-.

Workup

  1. customThis compound was prepared
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford
  8. custom16.4 g (61) of the title compound following recrystallization (acetone/water)

Sources & evidence

ORD record
ord-b8b70703deac4ded93d5efb4e749d480
Source dataset
uspto-grants-1999_09
Patent number
US05952328

Reaction notes

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