Toluene → HCID 69506815, compound

HRID 2366694Notes

Reaction equation

HRID 2366694 reaction equation
[OH-].[Na+].[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:4][CH3:5].C1(C)C=CC=CC=1>C(O)C>[CH2:3]([C:6]1[N:7]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 57455398HCID 57455398, compound

Product 1

HCID 69506815HCID 69506815, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous sodium hydroxide (2.4 mL of 6 M) was added to a solution of ethyl 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanoate (2.37 g, 7.26 mmol) in ethanol (25 mL); the reaction was stirred at ambient temperature for two hours and concentrated under reduced pressure. The residue was dissolved in water (15 mL) and adjusted to pH 4 with the addition of 2 M hydrochloric acid. A precipitate formed, was isolated by filtration, and was mixed with toluene, which was removed under reduced pressure to provide 1.78 g of 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanoic acid as a tan powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (15 mL)
  3. additionadjusted to pH 4 with the addition of 2 M hydrochloric acid
  4. customA precipitate formed
  5. customwas isolated by filtration
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-f4e897e89a1c467a9d7f3ee66ddfff8d
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…