Water → HCID 54265177, compound

HRID 2379709Notes

Reaction equation

HRID 2379709 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([CH:19](O)[CH:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:21]#[N:22])[C:10]2=[O:30])[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>ClCCl>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([CH:19]=[C:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:21]#[N:22])[C:10]2=[O:30])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 15230458HCID 15230458, compound

Product 1

HCID 54265177HCID 54265177, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g of 3-[1-(3,5-dichlorophenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-3-hydroxy-2-(3-pyridyl)propionitrile are suspended in 20 ml of dichloromethane. After the addition of 1.05 ml of trifluoroacetic acid (2 eq), a yellow solution is obtained which becomes bright yellow with a rise in temperature after the addition of 1.44 ml of trifluoroacetic anhydride (1.5 eq). This solution is stirred for one hour and water is then added; the organic phase is decanted, washed with a 10% solution of sodium bicarbonate and then water and dried over magnesium sulfate. After concentration under vacuum, the solid obtained is washed with ether and dried to give 2.6 g of 3-[1-(3,5-dichlorophenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-2-(3-pyridyl)prop-2-enenitrile in the form of a bright yellow solid melting at 261° C. Yield 91%.

Workup

  1. customa yellow solution is obtained which
  2. customthe organic phase is decanted
  3. washwashed with a 10% solution of sodium bicarbonate
  4. dry with materialwater and dried over magnesium sulfate
  5. concentrationAfter concentration under vacuum
  6. customthe solid obtained
  7. washis washed with ether
  8. customdried

Sources & evidence

ORD record
ord-9d2e73855d6141d1915aaf2d478726b6
Source dataset
uspto-grants-1994_11
Patent number
US05364860

Reaction notes

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