Hydrochloric Acid → 6-Fluoro-3-nitro-2-phenylaminobenzoic acid

HRID 242975

反応式

HRID 242975 の反応式
F[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1[C:4]([OH:6])=[O:5].CCN(CC)CC.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>CCO.O>[F:14][C:7]1[C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8471TriethylamineHCID 3026292,6-Difluoro-3-nitrobenzoic acid

生成物 1

HCID 681578336-Fluoro-3-nitro-2-phenylaminobenzoic acid収率 88.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2,6-difluoro-3-nitrobenzoic acid (5 g, 24.6 mmol) in EtOH (25 mL) and water (25 mL) at 0° C. were added Et3N (6.2 mL, 44.3 mmol) and aniline (2.3 g, 24.6 mmol). The reaction mixture was heated at 70° C. for 4 h under a nitrogen atmosphere. After cooling to RT, the pH of the solution was adjusted to 1 by addition of 1N HCl. A precipitate formed and this solid was collected by filtration, washed with water to afford the title compound (6.0 g, 88%). 1H NMR (DMSO-d6, 400 MHz): δ 9.02 (1H, s), 8.18 (1H, dd, J=9.29, 5.78 Hz), 7.25-7.16 (2H, m), 7.05 (1H, t, J=9.07 Hz), 7.00-6.91 (3H, m)

後処理

  1. temperatureAfter cooling to RT
  2. customA precipitate formed
  3. filtrationthis solid was collected by filtration
  4. washwashed with water

出典と根拠

ORDレコード
ord-f5dd1bd6282d49a9a691cc23366e4cc7
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

関連ノート

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