Sodium Hydroxide → 1-Oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid

HRID 577516Notes

Reaction equation

HRID 577516 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([O:12][CH:13]([CH3:15])[CH3:14])[CH:8]=[C:7]([C:16]([O:18]C)=[O:17])[C:6]=2[CH2:5][CH2:4][NH:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([O:12][CH:13]([CH3:14])[CH3:15])[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6]=2[CH2:5][CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86723679Methyl 1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

Product 1

HCID 867237431-Oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (Cpd E, 1.00 g, 3.80 mmol) in MeOH (20 mL) was added NaOH (3.00 mL, 12.0 mmol). The resulting reaction mixture was stirred at 50° C. for 3 hours. Volatiles were removed under vacuum and the resulting residue was dissolved in MeOH (30 mL), and neutralized with 1 M HCl to pH=2˜3. Precipitates were formed, collected by filtration, washed with water, and dried in an oven at 60° C. under vacuum to give 1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid (77a, 918 mg, 97%) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. customVolatiles were removed under vacuum
  3. dissolutionthe resulting residue was dissolved in MeOH (30 mL)
  4. customPrecipitates
  5. customwere formed
  6. filtrationcollected by filtration
  7. washwashed with water
  8. customdried in an oven at 60° C. under vacuum

Sources & evidence

ORD record
ord-4ddb1c64adc74c308be39df4cad0f8da
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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