Isatoic Anhydride → 2-amino-benzoic acid N'-(2-fluoro-phenyl)-hydrazide

HRID 1723853

반응식

HRID 1723853 반응식
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].C(N(CC)CC)C.[NH:18]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21](=O)[O:20]C1=O>C(O)C>[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH:10][C:21](=[O:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:18]

참가 물질

5

반응물 3

HCID 8359Isatoic AnhydrideHCID 8471TriethylamineHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)

생성물 1

HCID 685332472-amino-benzoic acid N'-(2-fluoro-phenyl)-hydrazide수율 40.4%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
21 °C

실험 절차

A stirred suspension of 845 g (5.03 mole) of 97% (2-fluoro-phenyl)-hydrazine, hydrochloride in 7.6 L of ethanol at 21-22° C. was added in a stream 563 g (5.57 mole) of triethylamine over a 20 minute period. A whitish gas formed initially. The resulting dark mixture was stirred at 21° C. for 20 minutes and then 854 g (5.03 mole) of 96% 1H-benzo[d][1,3]oxazine-2,4-dione was added. The resulting mixture was heated up to reflux (78° C.) over the next 1 hour. During this period, vigorous gas evolution was noted. Reflux was maintained for 2 hours and then the suspension was stirred at room temperature for 16 hours. The solid was collected by filtration, rinsed once with 150 mL of ethanol, then once with 150 mL of ethanol: ethyl acetate (1:1), and pressed dry under suction. Further drying in vacuo at 35° C. for 7 hours provided 498 g (40%) of product. A second crop of 51 g (4%) of material was obtained from the mother liquor.

후처리

  1. customA whitish gas formed initially
  2. temperatureThe resulting mixture was heated up
  3. temperatureto reflux (78° C.) over the next 1 hour
  4. waitDuring this period
  5. temperatureReflux
  6. temperaturewas maintained for 2 hours
  7. stirringthe suspension was stirred at room temperature for 16 hours
  8. filtrationThe solid was collected by filtration
  9. washrinsed once with 150 mL of ethanol
  10. dry with materialonce with 150 mL of ethanol: ethyl acetate (1:1), and pressed dry under suction
  11. customFurther drying in vacuo at 35° C. for 7 hours

출처 및 근거

ORD 기록
ord-d29f2915294d459e9cb835d9c9e2d19f
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485636B2

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