2-Methoxybenzylamine → (5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine

HRID 1170070Notes

Reaction equation

HRID 1170070 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](Cl)=[N:7]2.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18]>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:18][CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[O:14][CH3:13])=[N:7]2

Participants

3

Reactant 2

HCID 812922-MethoxybenzylamineHCID 142210335-Bromo-2-chloroquinoline

Product 1

HCID 67334552(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine

Procedure

5-Bromo-2-chloroquinoline (CAS 99455-13-7, 2.4 g, 10 mmol) and 2-methoxybenzylamine (2.7 g, 20 mmol) were stirred in a sealed tube at 120° C. for 3 days. The reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). (5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine was obtained as a light yellow solid (2.3 g, 67%), MS: m/e=343.1, 345.0 (M+H+).

Workup

  1. customThe reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)

Sources & evidence

ORD record
ord-1c45995ef84142c6aa18eac8effd7ac9
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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