Hydrochloric Acid → HCID 20515464, compound

HRID 1902473Notes

Reaction equation

HRID 1902473 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]([CH3:17])[C:11]=1[C:18]([OH:20])=O>O>[CH3:17][N:12]1[C:11]2[C:18](=[O:20])[NH:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[NH:9][C:10]=2[C:14]([CH3:15])=[C:13]1[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20515428HCID 20515428, compound2×

Product 1

HCID 20515464HCID 20515464, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

15 ml of concentrated hydrochloric acid are added to the solution obtained in Example 4, which contains 49.2 g (0.19 mole ) of 3-[(2-aminophenyl)amino]-1,4,5-trimethyl-1H-pyrrole-2-carboxylic acid, and the mixture is heated to an internal temperature of 140° C. for 12 hours. During this heating, the water formed is continuously distilled off. For working up the mixture, as much of the solvent as possible is distilled off on a rotary evaporator under a water-pump vacuum. The residue is taken up in 100 ml of water, and the mixture is adjusted to pH 2, at 80° C., with concentrated hydrochloric acid. The mixture is cooled to 0° C., with stirring. The precipitate formed is filtered off. The filtrate is extracted 3 times with 50 ml of ethyl acetate each time. The combined filtrates are dried with sodium sulfate and concentrated, and the residue is again taken up in 50 ml of water. The resulting mixture is adjusted to pH 2, at 80° C., with concentrated hydrochloric acid. After the mixture has been cooled to 0° C. in an ice-bath, it is filtered. The combined residues on the filter are washed with water and recrystallized from ethyl acetate.

Workup

  1. distillationis continuously distilled off
  2. distillationas much of the solvent as possible is distilled off on a rotary evaporator under a water-pump vacuum
  3. customis adjusted to pH 2, at 80° C., with concentrated hydrochloric acid
  4. temperatureThe mixture is cooled to 0° C.
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. extractionThe filtrate is extracted 3 times with 50 ml of ethyl acetate each time
  8. dry with materialThe combined filtrates are dried with sodium sulfate
  9. concentrationconcentrated
  10. customis adjusted to pH 2, at 80° C., with concentrated hydrochloric acid
  11. temperatureAfter the mixture has been cooled to 0° C. in an ice-bath
  12. filtrationit is filtered
  13. washThe combined residues on the filter are washed with water
  14. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-72e4a26f8a7a42838c6abb6be4518907
Source dataset
uspto-grants-1982_12
Patent number
US04363816

Reaction notes

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