8-Bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylic acid → 8-bromo-N-(4-methoxybenzyl)quinolin-4-amine

HRID 1469740Notes

Reaction equation

HRID 1469740 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8](C(O)=O)=[C:7]2[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 866922348-Bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylic acid

Product 1

HCID 866922358-bromo-N-(4-methoxybenzyl)quinolin-4-amineYield 101.6%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 8-bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylic acid (1.0 g, 2.58 mmol) in diphenyl ether (5 mL) was heated at 240° C. for 30 min. Then petroleum ether was added to the reaction mixture at rt and the precipitated solid was filtered and dried to afford 900 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.38 (d, J=5.4 Hz, 1H), 8.34-8.31 (d, J=9.0 Hz, 1H), 8.06 (t, 1H), 8.02-7.99 (d, J=7.5 Hz, 1H), 7.37-7.29 (m, 3H), 6.90-6.87 (d, J=8.4 Hz, 2H), 6.44 (d, J=5.1 Hz, 1H), 4.49 (d, J=6.0 Hz, 2H), 3.71 (s, 3H).

Workup

  1. filtrationthe precipitated solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-181b20f5156041019c5acbad86612801
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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