Dimethylamine → HCID 86683193, compound

HRID 1852109Notes

Reaction equation

HRID 1852109 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](F)=[CH:9][CH:10]=2)[C:5]([O:13][CH3:14])=[CH:4][N:3]=1.[CH3:15][NH:16][CH3:17].C1COCC1>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:16]([CH3:17])[CH3:15])=[CH:9][CH:10]=2)[C:5]([O:13][CH3:14])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 86683191HCID 86683191, compound

Product 1

HCID 86683193HCID 86683193, compoundYield 70%

Conditions

Temperature
100 °C

Procedure

To 1-chloro-6-fluoro-4-methoxyisoquinoline (200 mg, 0.945 mmol) was added dimethylamine 2 M in THF (2 ml, 4.00 mmol) and the solution was heated to 100° C. in a sealed tube for 16 h. The reaction was cooled and the volatiles were removed under vacuum. The crude residue was purified by silica gel chromatography using DCM as eluent. The product factions were collected and the solvent removed under vacuum to give 1-chloro-4-methoxy-N,N-dimethylisoquinolin-6-amine (150 mg, 70% yield). MS m/z 237.1 (M++1).

Workup

  1. temperatureThe reaction was cooled
  2. customthe volatiles were removed under vacuum
  3. customThe crude residue was purified by silica gel chromatography
  4. customThe product factions were collected
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-d8b962ed65ce4c58b9d3e1fe6ca81920
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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