Lithium Hydroxide → HCID 68294980, compound

HRID 572523Notes

Reaction equation

HRID 572523 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=1[C:21]([O:23]C)=[O:22].[OH-].[Li+]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=1[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68295566HCID 68295566, compound

Product 1

HCID 68294980HCID 68294980, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(2,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinoline-3-carboxylate (30 g, 74.7 mmol) in tetrahydrofuran (THF) (400 mL) was treated with lithium hydroxide (8.94 g, 373 mmol) and stirred at reflux overnight. The mixture was concentrated and used crude in the next step (21.6 g, 94%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.81-14.14 (m, 1 H) 8.28-8.37 (m, 1 H) 7.62-7.69 (m, 1 H) 7.53-7.61 (m, 1 H) 7.13-7.19 (m, 1 H) 7.01-7.12 (m, 2 H) 6.82-6.91 (m, 1 H) 3.52 (s, 3 H) 2.34 (s, 3 H) 1.97 (s, 3 H); LC/MS (m/z) ES+=308 (M+1).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-3eb0f5a5d1f34de7831272b042b63493
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

Loading…