P-Anisidine → Ethyl 6-bromo-4-((4-methoxyphenyl)amino)quinoline-3-carboxylate

HRID 1042329Notes

Reaction equation

HRID 1042329 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:24]=1Cl)=[CH:22][C:21]([Br:26])=[CH:20][CH:19]=2)=[O:14])[CH3:11]>O1CCOCC1>[Br:26][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])=[C:24]2[NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 2764138Ethyl 6-bromo-4-chloroquinoline-3-carboxylate

Product 1

HCID 23735926Ethyl 6-bromo-4-((4-methoxyphenyl)amino)quinoline-3-carboxylateYield 101.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

p-Anisidine (0.43 g) and 6-bromo-4-chloroquinoline-3-carboxylic acid ethyl ester (1 g) were mixed in dioxane and irradiated in a microwave reactor at 150° C. for 30 minutes. The reaction mixture was diluted with petroleum ether. The solid product obtained was filtered and dried to give 1.3 g (100%) of ethyl 6-bromo-4-[(4-methoxyphenyl)amino]quinoline-3-carboxylate. 1H NMR (300 MHz, CDCl3) δ 11.41 (s, 1H, —NH—), 9.22 (s, 1H, aromatic), 8.20 (d, 1H, J=8.2 Hz, aromatic), 7.77 (d, 1H, J=8.2 Hz, aromatic), 7.64 (s, 1H, aromatic), 7.15 (d, 2H, J=8.1 Hz, aromatic), 6.99 (d, 2H, J=8.1 Hz, aromatic), 4.47 (q, 2H, J=7 Hz, —CH2—), 3.89 (s, 3H, —OCH3), 1.47 (t, 3H, J=7 Hz, —CH3); LC-MS (m/z) 401.0 (M+1).

Workup

  1. customirradiated in a microwave reactor at 150° C. for 30 minutes
  2. customThe solid product obtained
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-4363312b4bff4b9a9582b1b472545d61
Source dataset
uspto-grants-2013_10
Patent number
US08557843B2

Reaction notes

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