Hydrochloric Acid → HCID 86719366, compound

HRID 1844500Notes

Reaction equation

HRID 1844500 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:13]=[N:12]1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:13]=[N:12]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 86719367HCID 86719367, compound

Product 1

HCID 86719366HCID 86719366, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

900 mg of 2-(1-(2-fluoro-4-nitrophenyl)-1H-pyrazol-4-yl)pyridine (24f) was dissolved in 25 mL ethyl alcohol (95%), and then the mixture was heated to reflux. HCl (4N, 660 μL) was added to the mixture, and then Fe powder (886.5 mg) was added in batches over 15 minutes, under stirring and refluxing. TLC monitoring was performed to determine completion of the reaction, after which the mixture was cooled down to room temperature and buffered to pH 9-10 with a saturated Na2CO3 solution. Then, the iron sludge in the mixture was removed by vacuum filtration. The filtrate was rotary evaporated, dissolved with water (20 mL), and then extracted with ethyl acetate for three times. The combined organic phase was washed with diluted hydrochloric acid (5%) until the organic phase was free of fluorescence. Then, the combined water phase was buffered to be basic (pH>7) with a saturated sodium bicarbonate solution. The resultant solution was extracted with ethyl acetate for three times. The combined organic phase was dried and rotary evaporated to obtain 540 mg of a light brown solid, with a yield of 67.2%. Thus obtained crude product can be directly used for the next step without further purification.

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperaturerefluxing
  3. customcompletion of the reaction
  4. customThen, the iron sludge in the mixture was removed by vacuum filtration
  5. dissolutiondissolved with water (20 mL)
  6. extractionextracted with ethyl acetate for three times
  7. washThe combined organic phase was washed with diluted hydrochloric acid (5%) until the organic phase
  8. extractionThe resultant solution was extracted with ethyl acetate for three times
  9. customThe combined organic phase was dried
  10. customrotary evaporated

Sources & evidence

ORD record
ord-d133069a6e65411ea7017a0b0b4b3e89
Source dataset
uspto-grants-2015_02
Patent number
US08946436B2

Reaction notes

Loading…