Pyridine → 2-Cyclopropylamino-4,5-difluorobenzoic acid

HRID 973786

반응식

HRID 973786 반응식
Cl[C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:13]1([NH2:16])[CH2:15][CH2:14]1.N1C=CC=CC=1.[OH-].[Na+]>CN(C)C(=O)C.[Cu]I.O>[CH:13]1([NH:16][C:2]2[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:15][CH2:14]1

참가 물질

8

반응물 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 7371712-Chloro-4,5-difluorobenzoic acid

생성물 1

HCID 149974732-Cyclopropylamino-4,5-difluorobenzoic acid수율 41%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 31374Dimethylacetamide용매

반응 조건

온도
70 °C

실험 절차

To a 10 ml resealable pressure reaction flask equipped with a magnetic stirrer and teflon septum cap was charged a solution of 1.0 g (5.19 mmol) 2-chloro-4,5-difluorobenzoic acid, 792 μl (11.43 mmol) cyclopropylamine, 800 mg (4.15 mmol) copper (I) iodide and 630 μl (7.79 mmol) pyridine in 8.0 ml of N,N-dimethylacetamide. The flask was sealed and was heated to 70° C. during stirring for a period of 16 hours. The reaction mixture was allowed to cool to room temperature and was then added to 100 ml of water. The suspension was adjusted to pH 13 with sodium hydroxide solution and was stirred for 15 minutes at room temperature. The suspension was filtered and the filtrate was adjusted to pH 4.5 with concentrated aqueous HCl. Filtration of the resulting slurry provided 451 mg (41%) of 2-cyclopropylamino-4,5-difluorobenzoic acid; m.p.: 175°-176° C.

후처리

  1. customTo a 10 ml resealable pressure reaction flask
  2. customequipped with a magnetic stirrer
  3. customThe flask was sealed
  4. temperatureto cool to room temperature
  5. stirringwas stirred for 15 minutes at room temperature
  6. filtrationThe suspension was filtered
  7. filtrationFiltration of the resulting slurry

출처 및 근거

ORD 기록
ord-40065f8587374d72922736b1916a88c5
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064958

연결된 노트

불러오는 중…