Hydrochloric Acid → HCID 12673425, compound

HRID 127360Notes

Reaction equation

HRID 127360 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:19][C:20]1[C:21]([CH3:27])=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].Cl>>[CH3:27][C:21]1[C:20]([Cl:19])=[CH:26][CH:25]=[CH:24][C:22]=1[NH:23][C:2]1[C:7]([C:8]([O:10][CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 68943-Chloro-2-methylanilineHCID 12673422HCID 12673422, compound

Product 1

HCID 12673425HCID 12673425, compound

Conditions

Temperature
140 °C

Procedure

Into a suitable flask, pivaloyloxymethyl 2-chloro-3-pyridinecarboxylate prepared according to Example 2, supra (21.7 g) and 3-chloro-2-methylaniline (28.4 g) are charged. To begin the reaction the mixture is heated to 140° C. During the reaction the temperature of the reaction mixture rises to 190° C. When reaction is completed, the temperature diminishes. The reaction mixture is then cooled to room temperature. Diluted hydrochloric acid is added to the cooled mixture and the precipitated compound ground into small particles and suspended in the reaction mixture. The solid is separated by filtration and the cake washed with water. Then the washed solid is dissolved in hot methanol and recrystallized by cooling the methanolic solution. The crystallized product is separated and dried under vacuum, at a temperature of 40° C. Pivaloyloxymethyl 2-(2'-methyl-3'-chloro-anilino)-3-pyridinecarboxylate (m.p. 90°-91° C.) is so obtained, with a yield of 22.5 g (77.6% of theory).

Workup

  1. additionare charged
  2. customthe reaction the mixture
  3. customDuring the reaction the temperature of the reaction mixture
  4. customrises to 190° C
  5. customWhen reaction
  6. temperatureThe reaction mixture is then cooled to room temperature
  7. customThe solid is separated by filtration
  8. washthe cake washed with water
  9. dissolutionThen the washed solid is dissolved in hot methanol
  10. customrecrystallized
  11. temperatureby cooling the methanolic solution
  12. customThe crystallized product is separated
  13. customdried under vacuum, at a temperature of 40° C

Sources & evidence

ORD record
ord-c6c0e8031e5c4f698d05e45ccf050db1
Source dataset
uspto-grants-1981_03
Patent number
US04255581

Reaction notes

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