Sulfuric Acid → 4-Amino-3-chloro-6-(4-chlorophenyl)-5-fluoropicolinaldehyde

HRID 1503103Notes

Reaction equation

HRID 1503103 reaction equation
[Cl:1][C:2]1[C:3]([CH:24](OCC)[O:25]CC)=[N:4][C:5]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:6]([F:16])[C:7]=1[N:8]=C1C=CC(=O)C=C1.S(=O)(=O)(O)O.C(Cl)Cl>C(#N)C.O>[NH2:8][C:7]1[C:6]([F:16])=[C:5]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:4]=[C:3]([CH:24]=[O:25])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 867233544-((3-Chloro-6-(4-chlorophenyl)-2-(diethoxymethyl)-5-fluoropyridin-4-yl)imino)cyclohexa-2,5-dienone

Product 1

HCID 867233534-Amino-3-chloro-6-(4-chlorophenyl)-5-fluoropicolinaldehyde

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

In a typical reaction, 4-((3-chloro-6-(4-chlorophenyl)-2-(diethoxymethyl)-5-fluoropyridin-4-yl)imino)cyclohexa-2,5-dienone is treated with a 1 M (molar) solution of sulfuric acid in a mixture of acetonitrile/water. The mixture is heated at reflux until the reaction is complete. The mixture is added to methylene chloride, and the organic layer is separated, washed with brine and dried. The solvent is evaporated to provide crude 4-amino-3-chloro-6-(4-chlorophenyl)-5-fluoropicolinaldehyde.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux until the reaction
  3. customthe organic layer is separated
  4. washwashed with brine
  5. customdried
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-de715d442c2b449b9728bd875c554fe7
Source dataset
uspto-grants-2015_12
Patent number
US09212141B2

Reaction notes

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