2-Methoxybenzylamine → HCID 67334113, compound

HRID 1669696Notes

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].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20]>>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH:20][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[N:9]=1

Participants

Reactant 2

HCID 812922-Methoxybenzylamine

HCID 3192512-Chloro-5-nitroquinoline

Product 1

HCID 67334113HCID 67334113, compound

Procedure

5-Nitro-2-chloroquinoline (CAS 13067-94-2,3 g, 14 mmol) and 2-methoxy-benzylamine (4.2 g, 31 mmol) were stirred in a sealed tube at 120° C. overnight. The reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->30:70 gradient). (2-Methoxy-benzyl)-(5-nitro-quinolin-2-yl)-amine was obtained as a yellow solid (2.2 g, 50%), MS: m/e=310.1 (M+H+).

Workup

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

Sources & evidence

ORD record: ord-899134790d904bf98294136250f5e38e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989628B2

Reaction notes

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