Hydrochloric Acid → HCID 58288427, compound

HRID 1476092Notes

Reaction equation

HRID 1476092 reaction equation
[NH2:1][C:2]1[C:3]([CH3:19])=[C:4](/[CH:9]=[C:10](\[CH3:18])/[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].NC1C(C)=C(C=CC=1Cl)CC(=C)C(OC(C)(C)C)=O.[Mg].II.Cl.[OH-].[Na+]>CO>[NH2:1][C:2]1[C:3]([CH3:19])=[C:4]([CH2:9][CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 14798Sodium HydroxideHCID 5462224MagnesiumHCID 58288359HCID 58288359, compoundHCID 58288368HCID 58288368, compound

Product 1

HCID 58288427HCID 58288427, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.58 g (5.61 mmol) of a mixture of tert-butyl (2E)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylacrylate and tert-butyl 2-(3-amino-4-chloro-2-methylbenzyl)acrylate (Example 135A) in 5.0 ml of methanol was added to 354 mg (14.6 mmol) of magnesium turnings and a few grains of iodine. The mixture was stirred at RT (initially with cooling) overnight. 50 ml of 1 N hydrochloric acid were then added with ice-cooling. By addition of 10% strength aqueous sodium hydroxide solution, the pH of the mixture was then adjusted to about 10. The mixture was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The crude product gave, after chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1 to 40:1), 962 mg of the target product (60.5% of theory).

Workup

  1. temperaturewith cooling) overnight
  2. temperaturecooling
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac7fda5c25e547daa52f1694d88c7fe4
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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