Hydrochloric Acid → HCID 54551545, compound

HRID 35273Notes

Reaction equation

HRID 35273 reaction equation
[CH3:1][N:2]([CH2:13][CH2:14][CH2:15][N:16]([CH3:18])C)[C:3]([C:5]1[NH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)=[O:4].Cl.[OH2:20].[CH2:21](O)[CH3:22]>[Pd]>[CH3:1][N:2]([CH2:13][CH2:21][CH2:22][N:6]([CH3:7])[CH3:5])[C:3]([C:15]1[NH:16][CH:18]=[C:13]([N:2]([CH3:1])[C:3]([C:5]2[NH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=2)=[O:4])[CH:14]=1)=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 542538903-[N-methyl-4-nitro-pyrrole-2-carboxamido]propyldimethylamine

Product 1

HCID 54551545HCID 54551545, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The compound of example 1 (3.4 g) was dissolved in ethanol (40 ml) and diluted hydrochloric acid (20 ml) and reduced over a Pd catalyst (5% on carbon) under H2 pressure (50 psi) in a Parr apparatus. Water (20 ml) was added and the catalyst filtered off. The resulting solution was concentrated and the residue was dissolved in water (40 ml). Sodium bicarbonate (4 g) was added, followed by a solution of N-methyl-4-nitropyrrole-2-carboxylic acid chloride (2.8 g) in 20 ml of benzene. The resulting mixture was stirred for about 2 hours at room temperature and then was extracted with chloroform. The dried organic extracts were concentrated in vacuo and the residue was purified by column chromatography (CHCl3 75, EtOH95% 25, NH4OH 0.6) to give 4.7 g of 3-[N-methyl-4-(N-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido]propyl-dimethylamine as a yellow solid, m.p. 178°-180° C.

Workup

  1. filtrationthe catalyst filtered off
  2. concentrationThe resulting solution was concentrated
  3. dissolutionthe residue was dissolved in water (40 ml)
  4. additionSodium bicarbonate (4 g) was added
  5. extractionwas extracted with chloroform
  6. concentrationThe dried organic extracts were concentrated in vacuo
  7. customthe residue was purified by column chromatography (CHCl3 75, EtOH95% 25, NH4OH 0.6)

Sources & evidence

ORD record
ord-1715224bf0c540359d169445f3e1e3d2
Source dataset
uspto-grants-1988_08
Patent number
US04766142

Reaction notes

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