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

HRID 973786

反応式

HRID 973786 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 149974732-Cyclopropylamino-4,5-difluorobenzoic acid収率 41%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-40065f8587374d72922736b1916a88c5
出典データセット
uspto-grants-1991_11
特許番号
US05064958

関連ノート

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