2-Chloro-5-nitroquinoline → (R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine

HRID 2076304Notes

Reaction equation

HRID 2076304 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](Cl)=[N:9]2)([O-:3])=[O:2].[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>>[C@H:16]1([NH:15][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[CH:13][C:4]=3[N+:1]([O-:3])=[O:2])[N:9]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 3192512-Chloro-5-nitroquinolineHCID 2733933(R)-(-)-1-Aminoindan

Product 1

HCID 67096022(R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine

Procedure

5-Nitro-2-chloroquinoline (CAS 13067-94-2, 2.4 g, 11.5 mmol) and (R)-1-aminoindane (3.13 g, 23.5 mmol) were stirred in a sealed tube at 120° C. overnight. The reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). (R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine was obtained as a brown solid (2.67 g, 76%), MS: m/e=306.2 (M+H+).

Workup

  1. customThe reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

Sources & evidence

ORD record
ord-7ccb1f2759ba49aabb57b5164ccea342
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

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