Nitric Acid → HCID 178474263、化合物

HRID 1407186ノート

反応式

HRID 1407186 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:21]([O-])=O.[Na+].[CH3:25][C:26](=[O:31])[CH2:27][C:28](=[O:30])[CH3:29].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[C:28]([C:27](=[N:21][NH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1)[C:26](=[O:31])[CH3:25])(=[O:30])[CH3:29]

参加物

9

反応物 7

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 10340Sodium CarbonateHCID 312304-AminoacetanilideHCID 31261AcetylacetoneHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

生成物 1

HCID 178474263HCID 178474263、化合物収率 80.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
-6 °C

実験手順

N-(4-Aminophenyl)acetamide (1000 mg, 6.66 mmol) was added to a solution of 6 mL of phosphoric acid (85%) and 4 mL of nitric acid (65%) at −6° C. When the mixture reached to room temperature, it was cooled to −6° C. and solid sodium nitrite (460 mg, 6.66 mmol) was added during 10 min. Small piece of ice (50 g) was added into the solution. The mixture was added at 0° C. to a suspension of 2,4-pentanedione (666 mg, 6.66 mmol) and potassium acetate (40 g) in ethanol (400 mL). The solution was stirred for 15 min, and then was added to 250 mL of saturated Na2CO3 aqueous solution, extracted with dichloromethane, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give the title compound (1400 mg, 80% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.22 (3H, s), 2.48 (3H, s), 2.60 (3H, s), 7.22 (1H, brs), 7.38 (2H, d, J=8.8 Hz), 7.57 (2H, d, J=8.8 Hz), 14.84 (1H, s).

後処理

  1. customreached to room temperature
  2. extractionextracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d26c3ec8410242a7862aa3bdd0e7c7db
出典データセット
uspto-grants-2014_12
特許番号
US08916566B2

反応ノート

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