Sodium Chloride → HCID 54401037, compound

HRID 612143Notes

Reaction equation

HRID 612143 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]#[N:14])=[CH:8]2.CC[N:18]([CH:22]([CH3:24])[CH3:23])C(C)C.[Br:25][CH2:26]/[CH:27]=[CH:28]/[C:29](Cl)=[O:30].[Cl-].[Na+]>C1COCC1>[Br:25][C:26]1[CH:24]=[C:22]([NH:18][C:8]2[C:7]3[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([NH:15][C:29](=[O:30])[CH:28]=[CH:27][CH2:26][Br:25])[CH:6]=3)[N:11]=[CH:10][C:9]=2[C:13]#[N:14])[CH:23]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 11263885(E)-4-Bromo-2-butenoyl ChlorideHCID 86754955HCID 86754955, compound

Product 1

HCID 54401037HCID 54401037, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.05 g (2.8 mmol) of 4-[3-bromo-phenyl)amino]-8-methoxy-6-amino-3-quinolinecarbonitrile and 3.9 ml (22.4 mmol) of Hunig's base in 50 ml of dry THF at 0° C., with stirring, was added a THF solution containing 4.11 g (22.4 mmol) of 4-bromo crotonylchloride dropwise. The mixture was stirred for additional 1 hour at 0° C. 50 mL of saturated sodium chloride solution was added to the reaction mixture, then it was extracted with ethyl acetate. The ethyl acetate solution was dried over sodium sulfate and then the drying agent was filtered off. This solution was used without further characterization.

Workup

  1. stirringThe mixture was stirred for additional 1 hour at 0° C
  2. extractionit was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  4. filtrationthe drying agent was filtered off

Sources & evidence

ORD record
ord-48946e1f6c1a4a76bd710f91e64e3f05
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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