Sulfuric Acid → HCID 86723380, compound

HRID 508540Notes

Reaction equation

HRID 508540 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([F:14])=[C:12]([NH:15]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:11]=[C:10]([CH:35](OCC)[O:36]CC)[N:9]=2)=[C:4]([F:42])[C:3]=1[O:43][CH3:44].S(=O)(=O)(O)O.C(Cl)Cl>C(#N)C.O>[NH2:15][C:12]1[C:13]([F:14])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:43][CH3:44])[C:4]=2[F:42])[N:9]=[C:10]([CH:35]=[O:36])[CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 86723379HCID 86723379, compound

Product 1

HCID 86723380HCID 86723380, compound

Reagents, catalysts & solvents 1

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

Procedure

In a typical reaction, 2-(4-chloro-2-fluoro-3-methoxyphenyl)-6-(diethoxymethyl)-3-fluoro-N-tritylpyridin-4-amine 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-6-(4-chloro-2-fluoro-3-methoxyphenyl)-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-0b35ac9e56a74c95b9a6385d47d58ef9
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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