Pyridine → HCID 5131202, compound

HRID 1734547Notes

Reaction equation

HRID 1734547 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 2× 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 2× with water
  3. washeluted with toluene
  4. washto elute
  5. customThe product was crystallized from MeOH which

Sources & evidence

ORD record
ord-e16ddc0806804c47998924ede9cde31d
Source dataset
uspto-grants-1996_07
Patent number
US05534521

Reaction notes

Loading…