Water → HCID 136094896, compound

HRID 2218256Notes

Reaction equation

HRID 2218256 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=[O:14])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25]CC2C=CC(OC)=CC=2)[N:3]=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.O>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[OH:25])[CH:5]=[C:6]([C:10]2[CH:18]=[CH:17][CH:16]=[C:12]([C:13]([OH:15])=[O:14])[CH:11]=2)[C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 59769653HCID 59769653, compound2×

Product 1

HCID 136094896HCID 136094896, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(2-amino-3-cyano-6-{2-[(4-methoxybenzyl)oxy]phenyl}-4-pyridinyl)benzoic acid (starting compound 5, 0.16 g, 0.36 mmol), trifluoroacetic acid (3.0 mL), anisole (0.50 mL), and water (0.50 mL) was stirred at room temperature overnight. The reaction mixture was diluted with toluene and concentrated under reduced pressure. The residue was dissolved in THF and then crystallized with hexane. The resulting precipitate was collected by filtration and washed with hexane, and then dried under reduced pressure to give 2-amino-6-(2-hydroxyphenyl)-4-(3-hydroxycarbonylphenyl)nicotinonitrile (0.12 g, yield 74%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in THF
  3. customcrystallized with hexane
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with hexane
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-aa12cc6c953b4ca289a477a403392a83
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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