تفاعل #2006410

ord-16f2c8cfa26d4881a2ce547cd7871669

معادلة التفاعل

Nc1ccc(CC(=O)O)cc1
4-aminophenylacetic acid
Cl
HCl
CO
methanol
COC(=O)Cc1ccc(N)cc1
3
المردود 74.0%
COC(=O)Cc1ccc(N)cc1
Methyl-4-aminophenylacetate
المردود 74.0%

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe reaction mixture was then quenched with a saturated aqueous solution of NaHCO3
  2. 2
    أخرىThe methanol was evaporated under reduced pressure
  3. 3
    استخلاصthe aqueous layer was extracted several times with AcOEt
  4. 4
    تجفيفThe combined organic extracts were dried over (MgSO4)
  5. 5
    أخرىevaporated
  6. 6
    أخرىThe crude residue was purified by flash chromatography

الإجراء التجريبي

To a solution of 4-aminophenylacetic acid (10 g, 66.2 mmol) in methanol (150 mL) at room temperature was added HCl conc. (37% 25 mL). The mixture became yellow and was stirred overnight. The reaction mixture was then quenched with a saturated aqueous solution of NaHCO3. The methanol was evaporated under reduced pressure and the aqueous layer was extracted several times with AcOEt. The combined organic extracts were dried over (MgSO4) and evaporated. The crude residue was purified by flash chromatography using hexane/AcOEt (4:1) as solvent mixture yielding 3 as a yellow oil (9.44 g, 74%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: USRE043343E1uspto-grants-2012_05