Potassium Carbonate → HCID 22496109, compound

HRID 1815924Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][CH2:22][NH:23]2)=[CH:18][CH:17]=1>C(C#N)(C)=O>[Cl:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][CH2:22][N:23]2[C:2]2[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of the compound 2,4-dichloro-1,3,5-triazine (1.0 g, 5.97 mmol) and solid K2CO3 (4.0 g, 29 mmol) was suspended in AcCN (20 mL) under nitrogen at 0° C., followed by slow addition of 7-chloro-1,2,3,4-tetrahydro-quinoline (Step 1) (1.1 g, 6.56 mmol) as a solution in AcCN (20 mL) over 15 min. The mixture was stirred at 0° C. for 1 h. The solids were removed by suction filtration and washed with AcCN. The organics were concentrated under reduced pressure and the crude compound was purified via column chromatography to give 7-chloro-1-(4-chloro-[1,3,5]triazin-2-yl)-1,2,3,4-tetrahydro-quinoline).

Workup

customThe solids were removed by suction filtration
washwashed with AcCN
concentrationThe organics were concentrated under reduced pressure
customthe crude compound was purified via column chromatography

Sources & evidence

ORD record: ord-0e6fca1caf334dde9045c0339c76f9d6
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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