2,6-Dichloroquinoline → HCID 57860969, compound

HRID 1931478Notes

Reaction equation

HRID 1931478 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.[NH2:13][C@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1>>[Cl:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:13][C@H:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15]1)[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 6075022,6-DichloroquinolineHCID 2733933(R)-(-)-1-Aminoindan

Product 1

HCID 57860969HCID 57860969, compoundYield 34%

Conditions

Temperature
125 °C

Procedure

A stirred mixture of 2,6-dichloro-quinoline (4.8 g, 24 mmol) and (R)-1-aminoindane (6.5 g, 48 mmol) was heated in a sealed tube for 16 h at 125° C. Purification by flash chromatography on silica gel (ethyl acetate/heptane) yielded (6-chloro-quinolin-2-yl)-(R)-indan-1-yl-amine as a yellow solid (2.4 g, 34%), MS 295.1 [(M+H)+].

Workup

  1. customPurification by flash chromatography on silica gel (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e6dc223e41a7409c9420c7f1115037d1
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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