Sodium Hydroxide → HCID 57733369, compound

HRID 1920737Notes

Reaction equation

HRID 1920737 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]=1[CH3:23])=[O:5])C.[OH-].[Na+]>CO.O>[CH3:23][C:7]1[N:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9](=[O:16])[C:10]2[C:15]([C:6]=1[C:4]([OH:5])=[O:3])=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57733276HCID 57733276, compound

Product 1

HCID 57733369HCID 57733369, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

3-Methyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester (4.2 g, 13.7 mmol) was dissolved in 100 ml of hot methanol and a solution of NaOH (6 g) in water (20 ml) was added. The reaction mixture was heated at reflux for 2 hrs, diluted with water (200 ml) and stirred overnight at ambient temperature. Organic volatiles were removed under reduced pressure and the obtained aqueous solution was extracted with ethyl acetate (2×50 ml). The aqueous solution was poured into ice/2M HCl (150 ml). The obtained suspension was sonicated, and the product was separated by filtration, washed with water and dried in vacuo to give 2.9 g of a colourless solid, yield 76%. LC-MS (m/z) 280.2 (MH+); tR=0.9. 1H NMR (500 MHz, DMSO-d6): 2.01 (s, 3H), 7.36 (d, 2H), 7.50 (t, 1H), 7.56 (q (overlapping m), 3H), 7.72 (d, 1H), 7.81 (t, 1H), 8.22 (d, 1H), 13.5 (br, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hrs
  3. customOrganic volatiles were removed under reduced pressure
  4. extractionthe obtained aqueous solution was extracted with ethyl acetate (2×50 ml)
  5. additionThe aqueous solution was poured into ice/2M HCl (150 ml)
  6. customThe obtained suspension was sonicated
  7. customthe product was separated by filtration
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a4b87a028f7546d686789e6bcab6b024
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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