4-Chloro-2-nitro-N-(propan-2-yl)aniline → HCID 19437878, compound

HRID 1734546Notes

Reaction equation

HRID 1734546 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][CH:7]([CH3:9])[CH3:8])=[C:4]([N+:12]([O-])=O)[CH:3]=1.[N+:15]([O-:18])(O)=[O:16].[C:19](OC(=O)C)(=[O:21])C>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[C:11]([N+:15]([O-:18])=[O:16])=[CH:10][C:5]2[N:6]([CH:7]([CH3:8])[CH3:9])[C:19](=[O:21])[NH:12][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 27366924-Chloro-2-nitro-N-(propan-2-yl)anilineHCID 22241977HCID 22241977, compound

Product 1

HCID 19437878HCID 19437878, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The compound of Example 4 (1.0 g, 5.0 mmol) was suspended in acetic anhydride (10 mL) and cooled in an ice bath. To this mixture was added dropwise 1.5 mL of a 1:2 mixture of nitric acid/acetic anhydride. The reaction mixture was stirred for 5 minutes before being poured into ice-water. The solid was filtered and washed well with water and suction-dried to afford 1.01 g (80%) of the title compound as a solid.

Workup

  1. temperaturecooled in an ice bath
  2. additionTo this mixture was added dropwise
  3. filtrationThe solid was filtered
  4. washwashed well with water
  5. customsuction-dried

Sources & evidence

ORD record
ord-5de67d1ef5bd48728f22d935007e5fa6
Source dataset
uspto-grants-1996_07
Patent number
US05534521

Reaction notes

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