P-Anisidine → HCID 59333347, compound

HRID 1893446Notes

Reaction equation

HRID 1893446 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][C:6]([C:16]([F:19])([F:18])[F:17])=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1>CN(C)C=O.Cl>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:33][C:32]2[CH:34]=[CH:35][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)[C:9]2[C:4](=[CH:5][C:6]([C:16]([F:19])([F:18])[F:17])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 59333294HCID 59333294, compound

Product 1

HCID 59333347HCID 59333347, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dichloro-3-nitro-7-trifluoromethyl-quinoline (220 mg; 0.70 mmol; 1 eq) in dimethylformamide (3.5 mL), are added successively triethylamine (105 μL; 0.76 mmol; 1.08 eq) and 4-methoxyaniline (88 mg; 712 mmol; 1.01 eq.). The reaction mixture is allowed to stir for 1 hour at room temperature until the reaction is complete on TLC. The crude solution is diluted with a 1M aqueous solution of HCl (5 mL) and then extracted with ethyl acetate (40 mL). The organic layer is separated and washed 3 times with a 1M aqueous solution of HCl (3×40 mL), dried over sodium sulfate, filtrated and concentrated under vacuum to afford the title compound as a yellow powder (280 mg; 0.70 mmol; 100%) which is used without further purification.

Workup

  1. extractionextracted with ethyl acetate (40 mL)
  2. customThe organic layer is separated
  3. washwashed 3 times with a 1M aqueous solution of HCl (3×40 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0f0f83def2f94366b5017d80299daf31
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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