Nitric Acid → N-(2-ethyl-6-nitrophenyl)acetamide

HRID 471613

反応式

HRID 471613 の反応式
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:6].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C.O>[CH2:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:1]([O-:4])=[O:2])[C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:6]

参加物

7

反応物 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 36332O-Ethylacetanilide

生成物 1

HCID 14147006N-(2-ethyl-6-nitrophenyl)acetamide収率 48%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒HCID 7918Acetic Anhydride溶媒

反応条件

温度
0 °C

実験手順

A solution of nitric acid (4.2 mL) in glacial acetic acid (5.2 mL)) was added drop wise to solution of N-(2-ethylphenyl)acetamide (Example 139f)(1.00 g, 6.13 mmol) in AcOH (22 mL) and acetic anhydride (18 mL) at 0° C. The reaction was stirred at 0° C. for 1 h, diluted with water (50 mL) and neutralized with Na2CO3 (pH˜8). The neutralized mixture was extracted with EtOAc (3×50 mL), the combined extract was washed with water and brine, and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified on HPLC to give 0.62 g (48%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.81 (broad s, 1H), 7.68-7.73 (m, 1H), 7.57-7.62 (m, 1H), 7.39 (t, J=8.0 Hz, 1H), 2.64 (q, J=8.0 Hz, 2H), 2.00 (s, 3H), 1.10 (t, J=8.0 Hz, 3H).

後処理

  1. extractionThe neutralized mixture was extracted with EtOAc (3×50 mL)
  2. extractionthe combined extract
  3. washwas washed with water and brine
  4. dry with materialdried with anhydrous MgSO4
  5. customThe filtrate was evaporated
  6. customthe residue was purified on HPLC

出典と根拠

ORDレコード
ord-a6b3bc18edfe4035bedbd1b424ea7342
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

関連ノート

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