Hydrochloric Acid → HCID 69056464, compound

HRID 227677Notes

Reaction equation

HRID 227677 reaction equation
[C:1]([C:4]1[NH:8][CH:7]=[C:6]([C:9]([OH:11])=[O:10])[C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)(=[O:3])[NH2:2].[H][H].[ClH:23]>CO.O1CCOCC1.[Pd]>[ClH:23].[C:1]([C:4]1[NH:8][CH:7]=[C:6]([C:9]([OH:11])=[O:10])[C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)(=[O:3])[NH2:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 577569005-carbamoyl-4-(4-nitrophenyl)-1H-pyrrole-3-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 69056464HCID 69056464, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 0.135 g (0.126 mmol) of 10% palladium-on-charcoal in 20 cm3 of methanol is added, at a temperature in the region of 20° C., 0.15 g (0.545 mmol) of 5-carbamoyl-4-(4-nitrophenyl)-1H-pyrrole-3-carboxylic acid. After hydrogenating for 3 hours in an autoclave under 3 bar of hydrogen, at a temperature in the region of 30° C., the reaction mixture is taken up in 5 cm3 of a 4N solution of hydrogen chloride in dioxane, and then filtered. The catalyst is rinsed with twice 2 cm3 of a 4N solution of hydrogen chloride in dioxane, and the filtrate is then concentrated to dryness under reduced pressure (2.7 kPa) to give 0.141 g of 5-carbamoyl-4-(4-aminophenyl)-1H-pyrrole-3-carboxylic acid hydrochloride in the form of a yellow solid; ES+: m/z=246: [M+H]+

Workup

  1. filtrationfiltered
  2. washThe catalyst is rinsed with twice 2 cm3 of a 4N solution of hydrogen chloride in dioxane
  3. concentrationthe filtrate is then concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-447878d9e63a4ad681d43f09255a0a21
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Reaction notes

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