HCID 86723761, compound → HCID 86723760, compound

HRID 577532Notes

Reaction equation

HRID 577532 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:27][CH:28]([CH3:30])[CH3:29])[C:5]([CH3:26])=[C:6]([CH:25]=1)[CH2:7][N:8]([CH2:19][CH:20](OC)OC)S(C1C=CC(C)=CC=1)(=O)=O>Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:27][CH:28]([CH3:30])[CH3:29])[C:5]([CH3:26])=[C:6]2[C:25]=1[CH:20]=[CH:19][N:8]=[CH:7]2

Participants

4

Reactant 1

HCID 86723761HCID 86723761, compound

Product 1

HCID 86723760HCID 86723760, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-[5-bromo-2-methyl-3-(propan-2-yloxy)benzyl]-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide (108d, 4.7 g, 9.4 mmol) in 6M HCl (75 mL) and 1,4-dioxane (75 mL) was stirred in a sealed tube at 50° C. for 18 hours. Volatiles were removed under vacuum and the aqueous solution was basified to pH 8˜9 with Na2CO3 (s). The mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (2×40 mL), dried over Na2SO4, filtered, and concentrated under vacuum to give 5-bromo-8-methyl-7-(propan-2-yloxy)isoquinoline (108e, 1.6 g, 61%) as a brown oil.

Workup

  1. customVolatiles were removed under vacuum
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with brine (2×40 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9db8f64d6b1e49fcb42887d193e73674
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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