Methanol → 4-bromo-N-ethylisoquinolin-1-amine

HRID 1922899

Reaction equation

HRID 1922899 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](Cl)=[N:4][CH:3]=1.CO.[CH2:15]([NH2:17])[CH3:16]>>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:17][CH2:15][CH3:16])=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6341EthylamineHCID 4597664-Bromo-1-chloroisoquinoline

Product 1

HCID 596052034-bromo-N-ethylisoquinolin-1-amineYield 88%

Conditions

Temperature
50 °C

Procedure

To a suspension of 4-bromo-1 chloroisoquinoline (0.831 g, 3.43 mmol) in MeOH (10.3 mL, 254 mmol) was added ethylamine (70% in water, 1.1 mL). The mixture was heated at 50° C. for 16 h. The mixture was concentrated. The residue was partitioned between water (20 mL) and DCM (20 mL). DCM layer was separated. The aqueous layer was extracted with DCM (10 mL) The combined DCM solutions were dried (Na2SO4). Filtration and concentration gave 4-bromo-N-ethylisoquinolin-1-amine (0.761 g, 88%). LCMS: M+H+=251.

Workup

  1. concentrationThe mixture was concentrated
  2. customThe residue was partitioned between water (20 mL) and DCM (20 mL)
  3. customDCM layer was separated
  4. extractionThe aqueous layer was extracted with DCM (10 mL) The combined DCM solutions
  5. dry with materialwere dried (Na2SO4)
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-ac312d68479d428696847172550e0583
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Linked notes

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