Nitric Acid → HCID 20378737, compound

HRID 2052105Notes

Reaction equation

HRID 2052105 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:16])[CH:5]=[C:6]([N:13]([CH3:15])[CH3:14])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[N+:17]([O-])([OH:19])=[O:18].O>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([CH3:16])[CH:5]=[C:6]([N:13]([CH3:14])[CH3:15])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 12290793HCID 12290793, compound2×

Product 1

HCID 20378737HCID 20378737, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Ethyl 6-chloro-4,N,N-trimethylanthranilate (compound 1) (3 g) was added dropwise with stirring to a solution of nitric acid (SG 1.43) (3 ml) in conc sulphuric acid (10 ml) at room temperature. The mixture was stirred overnight at room temperature, then poured into water (200 ml). The yellow product was extracted into chloroform, and the extracts were dried by filtration after washing with water. The solvent was removed and the residue crystallised from ethanol to give ethyl 6-chloro-4,N,N-trimethyl-5-nitroanthranilate (2 g) as yellow needles, mp 76° C.

Workup

  1. extractionThe yellow product was extracted into chloroform
  2. customthe extracts were dried by filtration
  3. washafter washing with water
  4. customThe solvent was removed
  5. customthe residue crystallised from ethanol

Sources & evidence

ORD record
ord-76581c3f28b24fb98421252c57c4150b
Source dataset
uspto-grants-1980_01
Patent number
US04182877

Reaction notes

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