Ethanol → 2,3-Dihydro-6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid

HRID 580302Notes

Reaction equation

HRID 580302 reaction equation
[CH:1]([C:4]1([CH3:22])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:15]=[C:14]3[O:16][CH:17]=[CH:18][C:13]3=[CH:12][C:11]=2[C:19]([OH:21])=[O:20])=[N:5]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(O)C.[H][H]>[Pd].O>[CH:1]([C:4]1([CH3:22])[C:8](=[O:9])[NH:7][C:6]([C:10]2[N:15]=[C:14]3[O:16][CH2:17][CH2:18][C:13]3=[CH:12][C:11]=2[C:19]([OH:21])=[O:20])=[N:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 137524676-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 137524792,3-Dihydro-6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acidYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid (1.7 g 0.056 mol) and 1.0 g (0.0072 mol) potassium carbonate in 200 mL 9:1 ethanol:water is added to 100 mg 5% palladium on carbon catalyst in a 500 mL pressure bottle. The bottle is fitted to a Parr hydrogenation apparatus, pressurized to 30 psi, with hydrogen, then shaken at room temperature for 10 hours. The catalyst is removed by filtration through a sintered glass funnel, and the filtrate concentrated in vacuo to 10 mL. Acidification of the residue to pH 2 gives a white precipitate which is removed by filtration, washed with water and air dried to give 1.0 g (63%) of 2,3-dihydro-6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)furo[2,3-b]pyridine-5-carboxylic acid as an off-white solid, mp 189°-192° C.

Workup

  1. customThe bottle is fitted to a Parr hydrogenation apparatus
  2. customThe catalyst is removed by filtration through a sintered glass funnel
  3. concentrationthe filtrate concentrated in vacuo to 10 mL
  4. customAcidification of the residue to pH 2 gives a white precipitate which
  5. customis removed by filtration
  6. washwashed with water and air
  7. customdried

Sources & evidence

ORD record
ord-4af6103d64364417b3fb6aecbb8d90a2
Source dataset
uspto-grants-1988_06
Patent number
US04752323

Reaction notes

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