Water → HCID 58158369, compound

HRID 2368827Notes

Reaction equation

HRID 2368827 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 4161 (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-56e06dc8ecac48ce9c2fbce5455077db
Source dataset
uspto-grants-2014_04
Patent number
US08703777B2

Reaction notes

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