(R)-(-)-1-Aminoindan → (6-nitro-quinolin-2-yl)-(R)-indan-1-yl-amine

HRID 1931482Notes

Reaction equation

HRID 1931482 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=2)[N:3]=1.[NH2:15][C@H:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1>>[N+:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:15][C@H:16]1[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17]1)[CH:11]=[CH:10]2)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 2733933(R)-(-)-1-AminoindanHCID 109217232-Chloro-6-nitroquinoline

Product 1

HCID 57860965(6-nitro-quinolin-2-yl)-(R)-indan-1-yl-amineYield 47%

Conditions

Temperature
125 °C

Procedure

A stirred mixture of 2-chloro-6-nitro-quinoline (2.2 g, 11 mmol) and (R)-1-aminoindane (2.8 g, 21 mmol) was heated in a sealed tube for 20 h at 125° C. Purification by flash chromatography on silica gel (ethyl acetate/heptane 0:1=>3:7) yielded (6-nitro-quinolin-2-yl)-(R)-indan-1-yl-amine as a brownish solid (1.5 g, 47%), MS 306.5 [(M+H)+].

Workup

  1. customPurification by flash chromatography on silica gel (ethyl acetate/heptane 0:1=>3:7)

Sources & evidence

ORD record
ord-431c548139114268a2a4b336e057ab87
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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