Ethylene Glycol → HCID 13138560, compound

HRID 2052154Notes

Reaction equation

HRID 2052154 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:3]=1.[CH3:22][NH:23][NH2:24].C(O)CO>O>[NH2:9][C:8]1[C:7]2[C:2](=[N:3][C:4]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:5][C:6]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:23]([CH3:22])[N:24]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6061MethylhydrazineHCID 13138484HCID 13138484, compound

Product 1

HCID 13138560HCID 13138560, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture consisting of 3.0 gm (0.01 mol) of 2-chloro-6-morpholino-4-phenyl-3-cyano-pyridine, 1.4 gm (0.03 mol) of methyl-hydrazine and 4 ml of ethylene glycol was refluxed for 3 hours at 170° C. (bath temperature). The resulting solution was then taken up in 50 ml of water, whereupon the reaction product initially separated out as a pasty precipitate. The pasty product was collected and digested with water, and after it has solidified it was suction-filtered off, washed and dried, yielding 2.8 gm (91% of theory) of the compound of the formula ##STR7## After recrystallizing the product over from methanol it had a melting point of 149°-152° C.

Workup

  1. custominitially separated out as a pasty precipitate
  2. customThe pasty product was collected
  3. filtrationwas suction-filtered off
  4. washwashed
  5. customdried
  6. customyielding 2.8 gm (91% of theory) of the compound of the formula
  7. custom##STR7## After recrystallizing the product over from methanol it

Sources & evidence

ORD record
ord-91866cab9a53497cb4d4e7a10f7e58fa
Source dataset
uspto-grants-1980_01
Patent number
US04182887

Reaction notes

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