تفاعل #657348

معادلة التفاعل

toluene

2-methyl-6-(methyloxy)-4H-3,1-benzoxazin-4-one

4-chlorophenylmagnesium bromide

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title compound

[2-amino-5-(methyloxy)phenyl](4-chlorophenyl)methanone

المذيبات

ether

ظروف التفاعل

المعالجة

1. 1
   أخرىat 0° C.
2. 2
   أخرىbefore being quenched with 1N HCl
3. 3
   استخلاصThe aqueous layer was extracted with EtOAc (3×)
4. 4
   غسيلthe combined organics were washed with brine
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   workup.DISSOLUTIONThe crude compound was then dissolved in EtOH (400 mL)
9. 9
   workup.ADDITION6N HCl (160 mL) was added
10. 10
    درجة الحرارةThe reaction mixture was refluxed for 2 h
11. 11
    تركيزbefore being concentrated under reduced pressure
12. 12
    ترشيحThe resulting solid was filtered
13. 13
    غسيلwashed twice with ether
14. 14
    استخلاصThe aqueous layer was extracted with EtOAc (3×)
15. 15
    غسيلthe combined organics were washed with brine
16. 16
    تجفيفdried over Na2SO4
17. 17
    ترشيحfiltered
18. 18
    تركيزconcentrated under reduced pressure

الإجراء التجريبي

To a solution of 2-methyl-6-(methyloxy)-4H-3,1-benzoxazin-4-one (for a preparation see Intermediate 8) (40.0 g, 0.21 mol) in a toluene (560 mL)/ether (200 mL) mixture at 0° C. was added dropwise a solution of 4-chlorophenylmagnesium bromide (170 mL, 1M in Et2O, 0.17 mol). The reaction mixture was allowed to warm to RT and stirred for 1 h before being quenched with 1N HCl. The aqueous layer was extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound was then dissolved in EtOH (400 mL) and 6N HCl (160 mL) was added. The reaction mixture was refluxed for 2 h before being concentrated under reduced pressure. The resulting solid was filtered and washed twice with ether before being suspended in EtOAc and neutralised with 1N NaOH. The aqueous layer was extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The title compound was obtained as a yellow solid (39 g, 88% yield) which was used without further purification.

المصدر