Реакция #84807

Уравнение реакции

2-methoxy-2-(quinolin-5-yl)acetic acid

NMM

isobutyl chloroformate

N,O-dimethylhydroxylamine hydrochloride

→

N,2-dimethoxy-N-methyl-2-(quinolin-5-yl)acetamide

Выход 60.0%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred for 15 min
2. 2
   Другоеthe ice bath was removed
3. 3
   workup.WAITAfter 24 hrs
4. 4
   workup.ADDITIONsaturated aqueous NaHCO3 was added
5. 5
   workup.STIRRINGstirred for 30 min
6. 6
   ДругоеThe layers were separated
7. 7
   Экстракцияthe aqueous layer was extracted with CH2Cl2
8. 8
   ПромывкаThe combined organics were washed with saturated aqueous NaHCO3, H2O and brine
9. 9
   Сушкаdried over Na2SO4
10. 10
    Концентрированиеconcentrated in vacuo
11. 11
    ДругоеPurification by chromatography (0-100% EtOAc-hexanes)

Методика

To an ice-cold solution of 2-methoxy-2-(quinolin-5-yl)acetic acid (2.8 g, 12.9 mmol) in anhydrous CH2Cl2 (50 mL) and NMM (3.1 mL, 29 mmol) under argon was added isobutyl chloroformate (1.9 mL, 14 mmol) dropwise. After stirring over an ice bath for 40 min, N,O-dimethylhydroxylamine hydrochloride (1.63 g, 16.8 mmol) was added in three aliquots over a period of 15 min. The mixture was stirred for 15 min then the ice bath was removed. After 24 hrs, saturated aqueous NaHCO3 was added and stirred for 30 min. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organics were washed with saturated aqueous NaHCO3, H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-100% EtOAc-hexanes) gave N,2-dimethoxy-N-methyl-2-(quinolin-5-yl)acetamide as an oil which became crystalline upon standing (1.8 g, 60% yield).

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