(R)-(-)-1-Aminoindan → HCID 68629716, compound

HRID 1931503Notes

Reaction equation

HRID 1931503 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11](Cl)[CH:10]=[CH:9]2)=[O:5])[CH3:2].[NH2:17][C@H:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19]1>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:17][C@H:18]1[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19]1)[CH:10]=[CH:9]2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 2733933(R)-(-)-1-AminoindanHCID 17834353Ethyl 2-chloroquinoline-6-carboxylate

Product 1

HCID 68629716HCID 68629716, compoundYield 95.4%

Conditions

Temperature
120 °C

Procedure

A stirred mixture of 2-chloro-quinoline-6-carboxylic acid ethyl ester [CAS-No. 29969-56-0] (500 mg, 2.12 mmol) and commercially available (R)-1-aminoindane (848 mg, 6.36 mmol) was heated in a sealed tube for 16 h at 120° C. Purification by flash chromatography on silica gel (ethyl acetate/heptane) yielded 2-((R)-indan-1-ylamino)-quinoline-6-carboxylic acid ethyl ester as a light brown solid (672 mg, 95%), MS (ISP) 333.2 [(M+H)+]; m.p. 137° C.

Workup

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

Sources & evidence

ORD record
ord-c587a4a2492544868ff621cdba59805e
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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