2-Methoxybenzylamine → (2-Methoxy-benzyl)-(6-nitro-quinolin-2-yl)-amine

HRID 1803074Notes

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.[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: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

Participants

Reactant 2

HCID 812922-Methoxybenzylamine

HCID 109217232-Chloro-6-nitroquinoline

Product 1

HCID 57647540(2-Methoxy-benzyl)-(6-nitro-quinolin-2-yl)-amine

Procedure

2-Chloro-6-nitro-quinoline (0.80 g, 4.0 mmol) and 2-methoxybenzylamine (1.5 mL, 12 mmol) were heated at 130° C. for 2 h. The reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate, 9:1, 4:1, 1:1). (2-Methoxy-benzyl)-(6-nitro-quinolin-2-yl)-amine was obtained as a yellow solid (0.5 g, 42%), MS: m/e=310.5 (M+H+).

Workup

customThe reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate, 9:1, 4:1, 1:1)

Sources & evidence

ORD record: ord-641367ff063a4f49bee10e8aa985836c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08350028B2

Reaction notes

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