Ammonia → HCID 20393022, compound

HRID 1862970Notes

Reaction equation

HRID 1862970 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=O.[C:13]1([NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19].CCCCOCCO.N>>[CH3:11][C:9]1[CH:8]=[C:7]([CH3:12])[C:3]2[C:4](=[O:6])[NH:20][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[NH:19][C:2]=2[N:10]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 7243O-PhenylenediamineHCID 81332-ButoxyethanolHCID 5911272-Chloro-4,6-dimethylnicotinic acid

Product 1

HCID 20393022HCID 20393022, compound

Conditions

Temperature
170 °C

Procedure

A mixture consisting of 9.3 gm of 2-chloro-4,6-dimethyl-nicotinic acid, 5.41 gm of o-phenylenediamine and 25 ml of butyl glycol was heated at 170° C. for 90 minutes while stirring. The mixture was subsequently cooled to 60° C. and poured over ice. After adjusting it to a pH-value of 8 with ammonia, the mixture was suction-filtered, and the filter cake was washed with water and recrystallized from aqueous 70% acetic acid, yielding 53% of theory of the compound named in the heading, which had a melting point of 297°-299° C.

Workup

  1. temperatureThe mixture was subsequently cooled to 60° C.
  2. additionpoured over ice
  3. filtrationthe mixture was suction-filtered
  4. washthe filter cake was washed with water
  5. customrecrystallized from aqueous 70% acetic acid
  6. customyielding 53% of theory of the compound

Sources & evidence

ORD record
ord-d9a13c7b640c4772a7494681b669d569
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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