Ammonia → HCID 20339594, compound

HRID 1395548Notes

Reaction equation

HRID 1395548 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8](Cl)[N:7]=1.[NH3:15].C(O)C>S([O-])([O-])(=O)=O.[Cu+2].CCOCC>[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([NH2:15])[N:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 20339507HCID 20339507, compound

Product 1

HCID 20339594HCID 20339594, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(2-dimethylaminoethylamino)-4-methyl-6-chloropyridine (from Example 77, Part A) (21.4 g., 0.1 mole), liquid ammonia (85 g) and copper sulfate catalyst (1.0 g) in 150 ml. ethanol is heated at 200° C. for 48 hours in a pressure vessel. The cooled reaction mixture is filtered and concentrated in vacuo. The residual oil is dissolved in 125 ml of chloroform, washed with excess sodium hydroxide and then with saturated sodium chloride solution, dried, filtered and concentrated in vacuo. The 16.0 g. of crude oil obtained is taken up in 100 ml of ether, filtered and extracted into dilute hydrochoric acid. The acidic extract is made basic and the product is extracted into ether. After drying and removing the ether in vacuo, the product (8.0 g.) is distilled. Purified material is collected at 125°-128° C. at 0.4 mm.

Workup

  1. customThe cooled reaction mixture
  2. filtrationis filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residual oil is dissolved in 125 ml of chloroform
  5. washwashed with excess sodium hydroxide
  6. dry with materialwith saturated sodium chloride solution, dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customof crude oil obtained
  10. filtrationfiltered
  11. extractionextracted into dilute hydrochoric acid
  12. extractionThe acidic extract
  13. extractionthe product is extracted into ether
  14. customAfter drying
  15. customremoving the ether in vacuo
  16. distillationthe product (8.0 g.) is distilled
  17. customPurified material is collected at 125°-128° C. at 0.4 mm

Sources & evidence

ORD record
ord-3c7b6a7fad8843e0901ee2b7d56fd933
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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