2-Phenoxyethanamine → 6-Chloro-N-(2-phenoxyethyl)-2-quinolinamine

HRID 1948988Notes

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

Participants

Reactant 2

HCID 156512-Phenoxyethanamine

HCID 6075022,6-Dichloroquinoline

Product 1

HCID 685743166-Chloro-N-(2-phenoxyethyl)-2-quinolinamine

Procedure

2,6-Dichloroquinoline (1.0 g, 5.1 mmol) and 2-phenoxyethylamine (1.5 g, 11 mmol) were microwaved at 120° C. for 1 h. The reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->70:30 gradient). (6-Chloro-quinolin-2-yl)-(2-phenoxy-ethyl)-amine was obtained as a light yellow solid (1.1 g, 73%), MS: m/e=299.3 (M+H+).

Workup

customThe reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->70:30 gradient)

Sources & evidence

ORD record: ord-70ce3e117fc843929c98253e726649cb
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399674B2

Reaction notes

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