Pyridine → HCID 135427889, compound

HRID 884722Notes

Reaction equation

HRID 884722 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C([O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=O)=[CH:17][CH:16]=1)(=O)C.N1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[OH:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]2[O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:9])[N:10]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 5147SalicylamideHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 135427889HCID 135427889, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Salicylamide (6.85 g, 50 mmol) and 4-acetoxybenzoyl chloride (10.9 g, 55 mmol) were dissolved in 35 mL anhydrous xylene. Anhydrous pyridine (0.5 mL) was added and the reaction mixture was refluxed under nitrogen for 12 h. Water was removed by a Dean-Stark apparatus. The mixture was cooled to rt, and the xylene was removed under vacuum. Acetone (100 mL) was added and the mixture was stirred for 10 min. The solid was filtered off, washed with acetone and dried under vacuum to give the crude compound (3.0 g). The crude compound (1.5 g) was purified by column chromatography (SilicaGel 70-230 mesh; 2-5% MeOH in DCM as eluent) to give 770 mg of 2-(4-hydroxyphenyl)benzo[e][1,3]oxazin-4-one (12%) as pale yellow solid. MS (ES) m/z: 240.02; Mp. 273-275° C.

Workup

  1. temperaturethe reaction mixture was refluxed under nitrogen for 12 h
  2. customWater was removed by a Dean-Stark apparatus
  3. customthe xylene was removed under vacuum
  4. additionAcetone (100 mL) was added
  5. filtrationThe solid was filtered off
  6. washwashed with acetone
  7. customdried under vacuum
  8. customto give the crude compound (3.0 g)
  9. customThe crude compound (1.5 g) was purified by column chromatography (SilicaGel 70-230 mesh; 2-5% MeOH in DCM as eluent)

Sources & evidence

ORD record
ord-2ad357a5885f49daae66ed7afc063ac6
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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