2,4-Dichloroaniline → 3-[(2,4-Dichlorophenyl)amino]isonicotinic acid

HRID 39499

反応式

HRID 39499 の反応式
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].F[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[C:17]([OH:19])=[O:18].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:15]1[CH:14]=[N:13][CH:12]=[CH:11][C:16]=1[C:17]([OH:19])=[O:18]

参加物

5

反応物 3

HCID 111232,4-DichloroanilineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 576496293-[(2,4-Dichlorophenyl)amino]isonicotinic acid収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2,4-Dichloraniline (162 mg, 1.00 mmol) and 3-fluoropyridine-4-carboxylic acid (141 mg, 1.00 mmol) were dissolved in dry THF (6.0 ml) under argon and the mixture was cooled to −78° C. A solution of LiHMDS (1.0M in THF, 3.5 ml) was added and the reaction mixture was allowed to warm to ambient temperature. After 18 h the reaction was quenched by adding a solution of HCl in dioxane (4.0M, 2.0 ml). The volatiles were removed in vacuo and the crude material was purified by flash chromatography using silica gel and a gradient of 0-10% methanol in DCM as eluent to give 204 mg (721 μmol; 72% yield) of pure desired product.

後処理

  1. temperatureto warm to ambient temperature
  2. customAfter 18 h the reaction was quenched
  3. additionby adding a solution of HCl in dioxane (4.0M, 2.0 ml)
  4. customThe volatiles were removed in vacuo
  5. customthe crude material was purified by flash chromatography

出典と根拠

ORDレコード
ord-1896779e9c5746ddb0e468683b4bf7d2
出典データセット
uspto-grants-2013_09
特許番号
US08524911B2

関連ノート

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