Acetic Acid → 2-amino-5-(trifluoromethoxy)benzoic Acid

HRID 393328

反応式

HRID 393328 の反応式
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9]C(=O)[C:7]2=[O:14].[OH-].[K+].OO.C(O)(=[O:23])C>O>[NH2:9][C:10]1[CH:11]=[CH:12][C:4]([O:3][C:2]([F:1])([F:16])[F:15])=[CH:5][C:6]=1[C:7]([OH:14])=[O:23]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14797Potassium Hydroxide2 回HCID 27327525-(trifluoromethoxy)-2,3-dihydro-1H-indole-2,3-dione

生成物 1

HCID 110853492-amino-5-(trifluoromethoxy)benzoic Acid収率 87%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

5-(Trifluoromethoxy)isatin (15.0 g, 65 mmol) and potassium hydroxide pellets (4 g) were mixed in water (35 mL) and cooled to 0° C. With vigorous stirring, a solution of 30% aqueous hydrogen peroxide (11.7 g), potassium hydroxide pellets (5.8 g), and water (80 mL) was added drop-wise keeping the temperature below 10° C. After stirring 1 hour at 0 C, glacial acetic acid (22 mL) was added drop-wise, causing foaming and formation of a precipitate. The contents were stirred overnight and filtered to afford the 2-amino-5-trifluoromethoxybenzoic acid as an amber solid (12.5 g, 87%). A small amount was recrystallized from ethyl acetate-hexanes to afford amber needles for an analytical sample and the remaining compound was used without further purification: mp 142.5-144.2° C. 1H NMR (CDCl3, 300 MHz) 7.98 (s, 1H), 7.18 (d, 1H, J=8.0 Hz), 6.62 (d, 1H, J=8.0 Hz), 6.40 (brs, 2H). Anal. Calc'd for C8H6NO3F3: C, 43.45; H, 2.73; N, 6.33. Found: C, 43.40; H, 2.65; N, 6.35.

後処理

  1. customthe temperature below 10° C
  2. additionwas added drop-wise
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-ac6960d965da462a9997d1fee0423cfd
出典データセット
uspto-grants-2004_10
特許番号
US06806288B1

関連ノート

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