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

HRID 1945726Notes

Reaction equation

HRID 1945726 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)
  5. dry with materialThe combined DCM solutions were dried (Na2SO4)
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-4ac34d4c131d4132895ea6819fd19128
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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