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Acetic Acid → 2-[4-(4-Pyridin-4-yl-isoxazol-5-yl)-phenoxymethyl]-quinoline

HRID 33834
Notes
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Reaction equation

HRID 33834 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:12][CH:11]=2)=O)=[CH:3][CH:2]=1.Cl.[OH:29][NH2:30].[C:31](O)(=O)C.C(=O)(O)[O-].[Na+]>COC(N(C)C)OC>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:31]=[N:30][O:29][C:8]=2[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:12][CH:11]=2)=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 336797272-(Pyridin-4-yl)-1-(4-(quinolin-2-ylmethoxy)phenyl)ethan-1-one

Product 1

HCID 116537552-[4-(4-Pyridin-4-yl-isoxazol-5-yl)-phenoxymethyl]-quinolineYield 45%

Reagents, catalysts & solvents 1

HCID 78373
Dimethylformamide dimethyl acetal
Solvent

Procedure

2-pyridin-4-yl-1-[4-(quinolin-2-ylmethoxy)-phenyl]-ethanone (200 mg, 0.56 mmole) was heated at reflux in dimethoxymethyl-dimethyl amine (1 ml) for 1 h and concentrated. The crude product was dissolved in methanol/water (3:1, 4 ml) and hydroxyl amine hydrochloride (43 mg, 1.1 eq.) was added. After 1 h, acetic acid was added (0.016 ml) and the reaction was heated at reflux for 1h. Cooled to ambient temperature poured into saturated sodium bicarbonate, extracted with methylene chloride, dried magnesium sulfate, filtered and concentrated. Biotage MPLC was run on a 25S column elution with 3% methanol/1% ammonium hydroxide/ethyl acetate 50% in hexanes to provide the title compound as a tan solid (94 mg, 45%). 1H NMR (400 MHz, CDCl3) δ 8.59(dd, J=6.2, 1.7 Hz, 2 H), 8.36 (s, 1H), 8.20 (d, J=8.3 Hz, 1H), 8.07 (d, J=8.7 Hz, 1 H), 7.82 (d, J=9.1 Hz, 1H), 7.73 (dt, J=7.1, 1.7 Hz, 1H), 7.64 (d, J=8.3 Hz, 1H), 7.54 (m, 3H), 7.28 (d, J=4.2 Hz, 2H) 7.05 (d, J=9.1, 2H), 5.40 (s, 2H); MS: (M+H m/z=380.2).

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude product was dissolved in methanol/water (3:1, 4 ml)
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 1h
  5. extractionextracted with methylene chloride, dried magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washBiotage MPLC was run on a 25S column elution with 3% methanol/1% ammonium hydroxide/ethyl acetate 50% in hexanes

Sources & evidence

ORD record
ord-8555a74987ca4c78a29f919bd5a12ab0
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429665B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes