Hydrochloric Acid → HCID 55281777, compound

HRID 2199584Notes

Reaction equation

HRID 2199584 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][NH:9][C:10]2[CH:15]=[C:14]([N:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][N:11]=2)C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[NH:9]([C:10]1[CH:15]=[C:14]([N:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][N:11]=1)[NH2:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86659953HCID 86659953, compound

Product 1

HCID 55281777HCID 55281777, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4.5 g (14.22 mmol) of 2-[2-(diphenylmethylidene)hydrazino]-N,N-dimethylpyridin-4-amine in 300 mL of toluene and 80 mL of aqueous 37% hydrochloric acid is heated for 4 hours at 110° C. After cooling to room temperature, the reaction medium is extracted with toluene (3×300 mL). The aqueous phase is diluted with 200 mL of water, neutralized at 0° C. by adding 12N sodium hydroxide solution, and then extracted with DCM (3×150 mL). The organic phases are combined, washed with brine (300 mL) and then dried over Na2SO4, filtered and concentrated under reduced pressure. 1.87 g of 2-hydrazino-N,N-dimethylpyridin-4-amine are obtained in the form of a brown solid, which is used without further purification in the following step.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction medium is extracted with toluene (3×300 mL)
  3. additionThe aqueous phase is diluted with 200 mL of water
  4. customneutralized at 0° C.
  5. additionby adding 12N sodium hydroxide solution
  6. extractionextracted with DCM (3×150 mL)
  7. washwashed with brine (300 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b1e765069cb345f8b59214d0318c3ed5
Source dataset
uspto-grants-2016_06
Patent number
US09359329B2

Reaction notes

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