Nitric Acid → 4-Fluoro-2-methyl-5-nitroaniline

HRID 599335

反応式

HRID 599335 の反応式
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1>OS(O)(=O)=O>[F:5][C:6]1[C:12]([N+:1]([O-:4])=[O:2])=[CH:11][C:9]([NH2:10])=[C:8]([CH3:13])[CH:7]=1

参加物

4

反応物 2

HCID 944Nitric AcidHCID 679824-Fluoro-2-methylaniline

生成物 1

HCID 190352714-Fluoro-2-methyl-5-nitroaniline収率 74%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
-10 °C

実験手順

Concentrated nitric acid (17 g, 0.18 mol) was added dropwise to a stirred solution of 4-fluoro-2-methylaniline (20 g, 0.16 mol) in cone H2SO4 (300 mL) at −10° C. The mixture was stirred at −10° C. for 10 min., and the reaction mixture was poured into ice water. The resultant solid was collected by filtration and partitioned between EtOAc and aq Na2CO3 solution (pH 8). The organic solution was washed with brine, dried (MgSO4) and concentrated to give 4-fluoro-2-methyl-5-nitroaniline (20 g, 74% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.27 (d, J=6.8 Hz, 1 H), 7.14 (d, J=12.4 Hz, 1 H) 5.37 (s, 2 H), 2.10 (s, 3 H).

後処理

  1. filtrationThe resultant solid was collected by filtration
  2. custompartitioned between EtOAc and aq Na2CO3 solution (pH 8)
  3. washThe organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d38e53abfed40418e574501f432404f
出典データセット
uspto-grants-2011_03
特許番号
US07897762B2

関連ノート

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