Hydrochloric Acid → HCID 23106772, compound

HRID 2376661Notes

Reaction equation

HRID 2376661 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13]CC)=[O:12])=[C:6]([NH:16][C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[C:6]([NH:16][C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86607069HCID 86607069, compound

Product 1

HCID 23106772HCID 23106772, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl (4-acetyl-2-{[(allyloxy)carbonyl]amino}phenyl)acetate (17.6 g) prepared by step e) and step f) was dissolved in ethanol (176 mL) and thereto was added at 0° C. 1M aqueous NaOH solution (132 mL), followed by stirring for 1 hour. To the reaction solution was added 2M hydrochloric acid (400 mL), and ethanol was removed in vacuo. The resulting solid was collected by filtration and washed with 2M hydrochloric acid, and dried in vacuo to give the object compound as a pale brown solid (11.2 g, 70%). Further the aqueous layer was extracted with ethyl acetate, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to give the object compound (3.58 g, 22%) as a brown solid.

Workup

  1. additionwas added at 0° C
  2. customwas removed in vacuo
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with 2M hydrochloric acid
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f808d10cfbed47269d7aaadcc0ae5e60
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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