2-Fluoro-4-nitrophenol → HCID 86650695, compound

HRID 1873685Notes

Reaction equation

HRID 1873685 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][CH3:20])=[C:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:32]=1[OH:40]>CN1CCCC1=O>[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[CH:33][C:32]=1[O:40][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:19][CH3:20])=[C:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 81531DiisopropylethylamineHCID 866506961,1-Dimethylethyl 4-chloro-7-methoxy-6-quinolinecarboxylate

Product 1

HCID 86650695HCID 86650695, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

Compound 1a (3.60 g) was dissolved in N-methylpyrrolidin-2-one (14 mL), and diisopropylethylamine (6.55 mL) and 2-fluoro-4-nitrophenol (2.89 g) were added to the solution. The mixture was heated to 140° C. and stirred for 4 hours. To the reaction mixture, distilled water was added on an ice bath, and the precipitate was filtrated, to thereby yield compound 1b (4.71 g, yield: 93%).

Workup

  1. distillationTo the reaction mixture, distilled water
  2. additionwas added on an ice bath
  3. filtrationthe precipitate was filtrated

Sources & evidence

ORD record
ord-4b5b741336a4406bbb24d54a24b5d587
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

Loading…