Pyridine → HCID 136274568, compound

HRID 1372139Notes

Reaction equation

HRID 1372139 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH:25]=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.Cl.[NH2:28][OH:29].N1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>CO.O>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([CH:25]=[N:28][OH:29])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 443297Hydroxyamine hydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 21071784HCID 21071784, compound

Product 1

HCID 136274568HCID 136274568, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-[4-(tert-butyldimethylsilanyloxy)-phenyl]-naphthalene-1-carbaldehyde (510 mg, 1.40 mmol), hydroxylamine hydrochloride (196 mg, 2.82 mmol), and anhydrous pyridine (0.228 ml, 2.82 mmol) in MeOH (3.2 ml) was heated to reflux for 3 h. The mixture was then concentrated under reduced pressure and dissolved in ether (5 ml). Then 1.0 M TBAF in THF (5.1 ml, 4.2 mmol) was added and stirred for 5 minutes. To the reaction was added water (5 ml) and then extracted with EtOAc. The organics were dried over anhydrous Na2SO4 and passed through a silica plug. Evaporation of the solvent and purification by column chromatography (10% MeOH-EtOAc) afforded 150 mg (41%) of product as a white solid: mp 200.0–200.5° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.93 (2H, d, J=8.0 Hz), 7.29 (2H, d, J=8.0 Hz), 7.42 (1H, d, J=7.3 Hz), 7.54 (1H, appt, J=7.6 Hz). 7.61 (1H, appt, J=7.6 Hz), 7.83 (1H, d, J=7.3), 7.92 (1H, d, J=8.4 Hz), 8.73 (1H, d, J=8.4 Hz), 8.81 (1H, s), 9.66 (1H,s), 11.45 (1H, s); MS (ESI) m/z 262 ([M−H]−).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. dissolutiondissolved in ether (5 ml)
  5. extractionextracted with EtOAc
  6. dry with materialThe organics were dried over anhydrous Na2SO4
  7. customEvaporation of the solvent and purification by column chromatography (10% MeOH-EtOAc)

Sources & evidence

ORD record
ord-b72f31597cfb4df39750a63b630302de
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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