Acetic acid methylene chloride → Methyl 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

HRID 494701ノート

反応式

HRID 494701 の反応式
[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])=[C:8]([Cl:19])[C:7]([N:20]=[N+]=[N-])=[N:6][CH:5]=1.ClCCl.C(O)(=O)C>[Zn].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])=[C:8]([Cl:19])[C:7]([NH2:20])=[N:6][CH:5]=1

参加物

5

反応物 2

HCID 21922555Acetic acid methylene chlorideHCID 59519382Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

生成物 1

HCID 59519500Methyl 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate収率 98%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8857Ethyl Acetate溶媒

実験手順

Zinc powder (10 g, 155 mmol) was added portionwise to a suspension of 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinic acid methyl ester (27) (12.94 g, 31 mmol) in 3:1 dichloromethane/acetic acid (300 mL). After fifteen minutes the reaction mixture was poured into 700 mL ethyl acetate, washed with water, saturated sodium bicarbonate and brine. The organic solution was dried over NaSO4, filtered, and concentrated in vacuo to provide the desired product (28) as an off-white solid (11.85 g, 98%). MS (APCI+) m/z 390, 392, 394 (M+; Cl, Br pattern) detected.

後処理

  1. washwashed with water, saturated sodium bicarbonate and brine
  2. dry with materialThe organic solution was dried over NaSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-48793d9a77984ef486ed13941ca4b84f
出典データセット
uspto-grants-2009_05
特許番号
US07538120B2

反応ノート

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