Sodium Hydroxide → (+/-)-2-(3-Phenoxybenzoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 1983562Notes

Reaction equation

HRID 1983562 reaction equation
C([O:3][C:4]([CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][N:7]1[C:16](=[O:30])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]=1)=[O:5])C.[OH-].[Na+]>C(O)C.O1CCCC1>[O:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[C:16]([N:7]1[CH:6]([C:4]([OH:5])=[O:3])[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68843784(+/-)-2-(3-Phenoxybenzoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester

Product 1

HCID 68844717(+/-)-2-(3-Phenoxybenzoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidYield 915.9%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a stirred solution of the product of step 1 (10.0 g, 2.50 mmol), in 1:1 ethanol/tetrahydrofuran (110 mL) was added 1.0 N aqueous sodium hydroxide solution (55 (mL). The mixture was stirred for 1 hour, concentrated and redissolved in water (150 (mL). While stirring, the solution was acidified with the addition of 1.0 N aqueous hydrochloric acid (55 mL). The resulting white precipitate was collected by filtration, rinsed with water and vacuum oven dried to afford 8.55 g (89%) of product as a white solid. In chloroform-d solvent, the proton NMR spectra of this compound appears as a 6:4 mixture of rotamers: 1H NMR (CDCl3) δ 7.44-6.78 (m, 13H), 5.29 (t, J=5.7 Hz, 0.6H), 5.18 (d, J=17.9 Hz, 0.4H), 4.81-4.73 (m, 0.4H), 4.62-4.47 (m, 1.6H), 3.30-3.15 (m, 1.6H), 3.13-3.01 (m, 0.4H) ppm.

Workup

  1. concentrationconcentrated
  2. dissolutionredissolved in water (150 (mL)
  3. stirringWhile stirring
  4. additionthe solution was acidified with the addition of 1.0 N aqueous hydrochloric acid (55 mL)
  5. filtrationThe resulting white precipitate was collected by filtration
  6. washrinsed with water and vacuum oven
  7. customdried

Sources & evidence

ORD record
ord-87413bb6c87e4a2ea645edf20af4c4ab
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

Loading…