Pyridine → HCID 5131202, compound

HRID 440917Notes

Reaction equation

HRID 440917 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[C:12](O)([C:14](F)(F)F)=O.N1C=CC=CC=1.CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH:7][CH2:12][CH3:14]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 6422Trifluoroacetic acid2×HCID 742185-Chloro-2-nitroaniline2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 5131202HCID 5131202, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-chloro-2-nitroaniline (17.2 g; 0.1 mole), acetalaldehyde diethyl acetal (Acetal) (21.1 ml; 0.15 mole) and TFA (7.7 ml; 0.1 moles) were dissolved in toluene (500 ml) and stirred for 1 hr. BH3 * pyridine (10.0 ml; 0.1 moles) was added in 1.0 ml increments. The reaction was exothermic, and the reaction progress was monitored by tlc 40%EtOAc/Hexane. Additional TFA, BH3 * pyridine and acetal were added until the tlc indicated that the 5-chloro-2-nitroaniline was consumed. The reaction mixture was washed 2X with water and placed on a bed of silica and eluted with toluene. The product was the first major component to elute. The product was crystallized from MeOH which produced 17.6 g (88%) of a yellow crystalline solid.

Workup

  1. customwas consumed
  2. washThe reaction mixture was washed 2X with water
  3. washeluted with toluene
  4. washto elute
  5. customThe product was crystallized from MeOH which

Sources & evidence

ORD record
ord-fb22ea3f33a54b378607c7d37aee5cd0
Source dataset
uspto-grants-1996_05
Patent number
US05521193

Reaction notes

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