Hydrochloric Acid → HCID 20515428, compound

HRID 1902472Notes

Reaction equation

HRID 1902472 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH3:8])[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)=[C:3]1[C:19]([O-:21])=[O:20].[K+].Cl.[H][H]>[Pd]>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:4]1[C:5]([CH3:8])=[C:6]([CH3:7])[N:2]([CH3:1])[C:3]=1[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20515473HCID 20515473, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20515428HCID 20515428, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The solution of 61 g (0.19 mole) of potassium 1,4,5-trimethyl-3-[(2-nitrophenyl)amino]-1H-pyrrole-2-carboxylate obtained in Example 3 is adjusted to pH 2 with concentrated hydrochloric acid in a circulatory hydrogenation apparatus, and 0.5 g of palladium-on-charcoal (10%) is added. When the internal temperature reaches 40° C., hydrogenation is started. Sufficient hydrogen is metered to keep the internal temperature at about 100° C. When a sudden drop in the absorption of hydrogen is observed, the solution is allowed to cool; it is filtered under nitrogen, and the residue on the filter is washed 6 times with 5 ml of 1-methyl-2-pyrrolidone each time. The combined filtrates are concentrated to half their volume on a rotary evaporator. The resulting solution is subsequently processed in Example 5 without further purification.

Workup

  1. additionis added
  2. customreaches 40° C.
  3. customat about 100° C
  4. customWhen a sudden drop in the absorption of hydrogen
  5. temperatureto cool
  6. filtrationit is filtered under nitrogen
  7. washthe residue on the filter is washed 6 times with 5 ml of 1-methyl-2-pyrrolidone each time
  8. concentrationThe combined filtrates are concentrated to half their volume on a rotary evaporator
  9. customThe resulting solution is subsequently processed in Example 5 without further purification

Sources & evidence

ORD record
ord-99cb363d381140dbb651d4bb2b7d7e40
Source dataset
uspto-grants-1982_12
Patent number
US04363816

Reaction notes

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