Acetic Acid → 2-Cyano-6-methylbenzoic acid

HRID 232867

反応式

HRID 232867 の反応式
N([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](C)[C:7]=1[C:13](O)=O.S(=O)(=O)(O)O.Cl.[C:22]([OH:25])(=[O:24])[CH3:23]>O>[C:6]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:13])[C:23]=1[C:22]([OH:25])=[O:24])#[N:5]

参加物

7

反応物 5

HCID 176Acetic Acid2 回HCID 313Hydrochloric AcidHCID 1118Sulfuric Acid2 回HCID 1512106-Methylanthranilic acidHCID 23668193Sodium Nitrite

生成物 1

HCID 570221172-Cyano-6-methylbenzoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

実験手順

Under ice cooling and stirring, 1.5 g of sodium nitrite dissolved in 2 ml of water was added dropwise over 1.5 hours to 3 g of 3-amino-o-toluic acid dissolved in a mixed solution of 8 ml of acetic acid, 8.3 g of sulfuric acid and 6.5 ml of water. After 3.2 ml of acetic acid, 0.4 g of sulfuric acid and 5.6 ml of water were added to the reaction mixture, the mixture was filtered and the reaction filtrate was adjusted. On the other hand, 6.5 g of potassium cyanide dissolved in 12.7 ml of water was added dropwise to 5.9 g of copper sulfate.pentahydrate dissolved in 12.7 ml of water at room temperature under stirring and 21.5 g of sodium hydrogen carbonate and 70 ml of toluene were added to the mixture. Under ice cooling and stirring, the above reaction filtrate was added dropwise to this 10 reaction mixture over 1 hour and then the mixture was stirred at 80° C. for 30 minutes. After completion of the reaction, the reaction mixture was adjusted to about pH 3 with 1N-hydrochloric acid, crystals precipitated were extracted with ethyl acetate and the organic layer was washed with a saturated saline solution and then dried over anhydrous sodium carbonate. The solvent was removed to obtain 3.8 g of the title compound. Mass (CI); m/z=162 (M+ +1)

後処理

  1. filtrationthe mixture was filtered
  2. dissolutionOn the other hand, 6.5 g of potassium cyanide dissolved in 12.7 ml of water
  3. additionwas added dropwise to 5.9 g of copper sulfate
  4. dissolutionpentahydrate dissolved in 12.7 ml of water at room temperature
  5. stirringunder stirring
  6. addition21.5 g of sodium hydrogen carbonate and 70 ml of toluene were added to the mixture
  7. stirringUnder ice cooling and stirring
  8. additionthe above reaction filtrate was added dropwise to this 10 reaction mixture over 1 hour
  9. stirringthe mixture was stirred at 80° C. for 30 minutes
  10. customAfter completion of the reaction
  11. customprecipitated
  12. extractionwere extracted with ethyl acetate
  13. washthe organic layer was washed with a saturated saline solution
  14. dry with materialdried over anhydrous sodium carbonate
  15. customThe solvent was removed

出典と根拠

ORDレコード
ord-f2c49aa6af8e4205899da96c87f76d5c
出典データセット
uspto-grants-1997_01
特許番号
US05591752

関連ノート

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