Hydrochloric Acid → 5-Chloro-2-methyl-4-nitrobenzonitrile

HRID 1739834ノート

反応式

HRID 1739834 の反応式
[Cl:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)N.Cl.N([O-])=O.[Na+].[C:18]([Cu])#[N:19].[C-]#N.[Na+]>CC(C)=O.O.CCOC(C)=O>[Cl:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[C:18]#[N:19]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 837726-Chloro-4-nitro-o-toluidineHCID 23668193Sodium NitriteHCID 178418546HCID 178418546、化合物

生成物 1

HCID 102417995-Chloro-2-methyl-4-nitrobenzonitrile収率 77.5%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒4 回HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 5-chloro-4-nitro-2-methylaniline (40.0 g, 0.21 mol) in acetone (140 mL) and H2O (150 mL) at 0° C. was added concentrated aqueous HCl (45 mL). The mixture was well stirred and a solution of NaNO2 (18.0 g, 0.26 mol) in H2O (60 mL) was added dropwise over a period of 15 min. The mixture was further stirred for 20 min. and then added portionwise to a vigorously stirred mixture of CuCN (30.0 g, 0.34 mol) and NaCN (44.0 g, 0.90 mol) in H2O (200 mL):EtOAc (100 mL). After stirring at room temperature for 30 min., the mixture was diluted with H2O and extracted with EtOAc. The EtOAc extract was washed successively with 1N NaOH and brine, dried over anhydrous MgSO4 and concentrated. The residue was suspended in hexanes:Et2O (1:1), stirred for 15 min., and filtered to provide the title compound (32 g, 76%) as yellow solid.

後処理

  1. stirringThe mixture was further stirred for 20 min.
  2. stirringAfter stirring at room temperature for 30 min.
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed successively with 1N NaOH and brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. stirringstirred for 15 min.
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-edf593854bda4ae59ef7fe5da95e23a0
出典データセット
uspto-grants-1999_10
特許番号
US05968958

反応ノート

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