Trifluoroacetic acid → HCID 22321557, compound

HRID 496552Notes

Reaction equation

HRID 496552 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1.O[CH2:14][C:15]([C:17]1[CH:21]=[C:20]([CH3:22])[O:19][N:18]=1)=O.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH3:22][C:20]1[O:19][N:18]=[C:17]([C:15]2[N:3]3[NH:4][C:5](=[O:12])[C:6]4[C:11]([C:2]3=[N:1][CH:14]=2)=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5951784-Amino-1(2H)-phthalazinoneHCID 22321558HCID 22321558, compound

Product 1

HCID 22321557HCID 22321557, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Amino-1-phthalazinone (2.28 g, 14.2 mmol) [Angew. (1967) 6(2) 173-4] and 2-hydroxy-1-(5-methylisoxazol-3-yl)ethanone (2.0 g, 14.2 mmol) were suspended in toluene (100 ml) and trifluoroacetic acid (5 ml) was added. The suspension was heated at reflux under Dean & Stark conditions, for 24 hours. The solvent was then removed in vacuo and the residue was purified by chromatography on silica gel eluting with 10% methanol:dichloromethane, to provide the title product (1.62 g, 43%), 1H NMR (360 MHz, d6-DMSO) 2.50 (3H, s), 5.96 (2H, br s), 7.79-8.22 (4H, m) 11.48 (1H, s).

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux under Dean & Stark conditions, for 24 hours
  3. customThe solvent was then removed in vacuo
  4. customthe residue was purified by chromatography on silica gel eluting with 10% methanol

Sources & evidence

ORD record
ord-e28354f1c9d44c1db0a0965ef092bfaa
Source dataset
uspto-grants-2005_09
Patent number
US06946461B2

Reaction notes

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