4,7-Dichloroquinoline → HCID 69921757, compound

HRID 2415621Notes

Reaction equation

HRID 2415621 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:13][C@@H:14]1[CH2:19][C@H:18]([NH2:20])[C@H:17]([CH3:21])[CH2:16][C@@H:15]1[NH2:22]>>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:20][C@H:18]3[CH2:19][C@@H:14]([CH3:13])[C@@H:15]([NH2:22])[CH2:16][C@H:17]3[CH3:21])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 68664,7-DichloroquinolineHCID 69922408HCID 69922408, compound

Product 1

HCID 69921757HCID 69921757, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 4,7-dichloroquinoline (500 mg, 2.5 mmol) and (1S,2R,4S,5R)-2,5-dimethylcyclohexane-1,4-diamine (750 mg, 5.2 mmol) was heated at 150° C. for 5 hours, cooled to room temperature, and flash chromatographed through silica gel column with dichloromethane and methanol (3:1 ratio by vol) to provide the titled compound. MS(ESI(+)Q1MS m/z 304 (M+H)+).

Workup

  1. temperaturecooled to room temperature
  2. customflash chromatographed through silica gel column with dichloromethane and methanol (3:1 ratio by vol)

Sources & evidence

ORD record
ord-9cc79395b0594bdb8281426829650606
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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