Ethylene Glycol → HCID 178509240, compound

HRID 27882Notes

Reaction equation

HRID 27882 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.O.[NH2:23][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)[NH:24][N:23]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24654Hydrazine hydrate (1:1)HCID 13138484HCID 13138484, compound

Product 1

HCID 178509240HCID 178509240, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture consisting of 15.0 gm (0.05 mol) of 2-chloro-6-morpholino-4-phenyl-3-cyano-pyridine (see Example C), 20 ml of 80% hydrazine hydrate and 100 ml of ethylene glycol was heated for 3 hours at 130° C. Thereafter, the resulting solution was poured into about 1 liter of water, whereupon a virtually colorless precipitate formed which was collected by suction filtration, washed with water and then immediately reprecipitated from 700 ml of 0.1 N hydrochloric acid with concentrated ammonia. The reprecipitated product was collected by suction filtration, washed and dried, yielding 13.7 gm (93% of theory) of practically pure 3-amino-6-morpholino-4-phenyl-1H-pyrazolo[3,4-b]pyridine, m.p. 178°-180° C., of the formula ##STR6## After recrystallization from ethanol it had a melting point of 180°-182° C.

Workup

  1. customformed which
  2. filtrationwas collected by suction filtration
  3. washwashed with water
  4. customimmediately reprecipitated from 700 ml of 0.1 N hydrochloric acid with concentrated ammonia
  5. filtrationThe reprecipitated product was collected by suction filtration
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-42296a518df446f19f2c6ef26c08f89c
Source dataset
uspto-grants-1980_09
Patent number
US04224322

Reaction notes

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