Hydrochloric Acid → HCID 15672410, compound

HRID 483620Notes

Reaction equation

HRID 483620 reaction equation
[C:1]([C:4]([NH:9][C:10]([C:12]1[N:20]=[CH:19][C:18]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])=O)([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].[OH-].[K+].Cl>C(Cl)Cl>[O:22]1[CH2:23][CH2:24][O:25][CH:21]1[C:18]1[CH:19]=[N:20][C:12]([C:10]2[NH:2][C:1](=[O:3])[C:4]([CH:5]([CH3:7])[CH3:6])([CH3:8])[N:9]=2)=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15672409HCID 15672409, compound

Product 1

HCID 15672410HCID 15672410, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]-5-(1,3-dioxolan-2-yl)nicotinic acid (4.19 g, 0.019 mol) and 15% potassium hydroxide is heated at 80° C. for 1 hour. The reaction mixture is acidified to pH 3 with concentrated hydrochloric acid and methylene chloride is added. The methylene chloride layer is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give an oil. The oil is chromatographed using silica gel and methylene chloride with increasing percentage of ether as eluent to give the title compound as a pale yellow solid (0.19 g, 5%), mp 156° C., identified by IR and NMR spectral analyses.

Workup

  1. additionis added
  2. customThe methylene chloride layer is separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil is chromatographed
  7. temperaturewith increasing percentage of ether as eluent

Sources & evidence

ORD record
ord-68e8456567254974b4249b3e4ae92417
Source dataset
uspto-grants-1993_07
Patent number
US05225564

Reaction notes

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