[(E)-1-(2-hydroxy-3-methylphenyl)ethylideneamino] acetate → 3,7-Dimethylbenzisoxazole

HRID 873882Notes

Reaction equation

HRID 873882 reaction equation
C(O/[N:5]=[C:6](/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[OH:15])\[CH3:7])(=O)C>N1C=CC=CC=1>[CH3:7][C:6]1[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=2[O:15][N:5]=1

Participants

3

Reactant 1

HCID 137014778[(E)-1-(2-hydroxy-3-methylphenyl)ethylideneamino] acetate

Product 1

HCID 124113243,7-DimethylbenzisoxazoleYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

(E)-1-(2-hydroxy-3-methylphenyl)ethanone O-acetyl oxime (Step 46.3) (6.0 g, 29.0 mmol) was dissolved in pyridine (60 mL) and the resulting mixture was heated up and stirred at 130° C. for 40 hr, cooled down to RT and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 0-50% EtOAc) to afford the title product (3.62 g, 23.12 mmol, 80% yield) as pale yellow oil. tR: 0.96 min (LC-MS 2); ESI-MS: 148 [M+H]+; Rf=0.56 (hexane/EtOAc 3:1).

Workup

  1. temperaturethe resulting mixture was heated up
  2. temperaturecooled down to RT
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc 0-50% EtOAc)

Sources & evidence

ORD record
ord-994b534ca3744b55a265c511f98cd102
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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