Hydrochloric Acid → HCID 23444588, compound

HRID 1840865Notes

Reaction equation

HRID 1840865 reaction equation
[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[O:9]C(=O)[NH:11][C:6]=2[CH:5]=[CH:4][C:3]=1[N:14]([CH3:16])[CH3:15].Cl.C([O-])(=O)C.[Na+]>[OH-].[Na+]>[NH2:11][C:6]1[C:7]([C:8]([OH:13])=[O:9])=[C:2]([CH3:1])[C:3]([N:14]([CH3:15])[CH3:16])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 23444604HCID 23444604, compound

Product 1

HCID 23444588HCID 23444588, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The product of Step A (1.20 g, 5.5 mmol) was suspended in 16.5 mL of 1N NaOH and stirred at room temperature for 1 hour. The pH was adjusted to 4 with 3N HCl and concentrated to near dryness under reduced pressure. The wet residue was suspended in EtOAc and treated with sodium acetate (1.30 g, 18 mmol). The EtOAc layer was dried (Na2SO4), filtered and evaporated under reduced pressure affording 641 mg (61%) of product. 1H-NMR (300 MHz, d6-DMSO) δ 2.18 (s, 3H), 2.46 (s, 6H), 6.35 (d. J=8 Hz, 1H), 6.67 (d. J=8 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. dry with materialThe EtOAc layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ca116bfa41e747e3bae3986ab1843b52
Source dataset
uspto-grants-2004_01
Patent number
US06683077B2

Reaction notes

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