Water → HCID 58158369, compound

HRID 1506095Notes

Reaction equation

HRID 1506095 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[C:8]([CH:20]=[O:21])=[CH:7]2.O.[CH2:23]1COCC1>>[OH:21][CH:20]([C:8]1[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:10](=[O:12])[C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1])[CH3:23]

Participants

4

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 58158302HCID 58158302, compound

Product 1

HCID 58158369HCID 58158369, compoundYield 71%

Conditions

Temperature
-78 °C

Procedure

8-Methyl-1-oxo-2-o-tolyl-1,2-dihydroisoquinoline-3-carbaldehyde 4101 (2.4 g, 8.6 mmol) was dissolved in anhydrous THF (280 mL) and cooled to −78° C. under a nitrogen atmosphere. Methyl MgBr (2 M, 5 mL, 10 mmol) was added slowly, and the resulting mixture was stirred at −78° C. for 2 h. H2O (5 mL) was added and then the solution was poured into ice-water (200 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue product was purified by flash column chromatography on silica gel (10-50% EA/PE) to afford the product, 3-(1-hydroxyethyl)-8-methyl-2-o-tolylisoquinolin-1(2H)-one 4102 (1.8 g, 71% yield) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue product was purified by flash column chromatography on silica gel (10-50% EA/PE)

Sources & evidence

ORD record
ord-aebd78ac498d44a2b4b286d06d72765a
Source dataset
uspto-grants-2015_12
Patent number
US09216982B2

Reaction notes

Loading…