تفاعل #5023

ord-fa8c1a5973204abeab956b536c71aec8

معادلة التفاعل

CCO
ethanol
CC(=O)N1CCc2cc(Br)cc([N+](=O)[O-])c21
N-acetyl-5-bromo-7-nitroindoline
Cl
hydrochloric acid
CC(=O)N1CCc2cc(Br)cc(N)c21
compound
المردود 32.2%
CC(=O)N1CCc2cc(Br)cc(N)c21
N-acetyl-7-amino-5-bromoindoline
المردود 32.2%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةto refluxing for 5 hours with vigorous stirring
  2. 2
    ترشيحThe reaction mixture was filtered by suction while hot
  3. 3
    أخرىto remove insoluble matter
  4. 4
    تركيزthe filtrate thereof was concentrated
  5. 5
    درجة الحرارةcooled

الإجراء التجريبي

To a mixed solution of ethanol (400 ml) and water (100 ml), were added N-acetyl-5-bromo-7-nitroindoline (133.1 g), iron powder (10 mesh; 75 g) and concentrated hydrochloric acid (5 ml), and the mixture was subjected to refluxing for 5 hours with vigorous stirring. The reaction mixture was filtered by suction while hot to remove insoluble matter, and then the filtrate thereof was concentrated and cooled on standing to give the intended compound 38.3 g (32.2%) as a brown needle crystal. M.P.: 154°-155° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05242912uspto-grants-1993_09