Hydrochloric Acid → HCID 10681402, compound

HRID 492238Notes

Reaction equation

HRID 492238 reaction equation
[CH2:1]([N:8]1[CH:16]([OH:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[OH-].[NH4+:24].Cl>ClCCl>[NH2:24][CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[O:17])[N:8]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 32407432-benzyl-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 10681402HCID 10681402, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol 20 (500 mg, 2.1 mmol) in dichloromethane at room temperature was added thionyl chloride (0.25 mL, 3.14 mmol) and the resulting reaction mixture is allowed to stir at room temperature for half hour. Thereafter concentrated ammonium hydroxide (10 mL) was added and the resulting reaction mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was poured onto 1N HCl and extracted with ethyl acetate (3×20 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography (SiO2, 35% EtOAc-Hexanes eluant) provided 310 mg of 24 as a white solid (500 mg theoretical, 62% yield).

Workup

  1. customthe resulting reaction mixture
  2. customthe resulting reaction mixture
  3. stirringto stir at room temperature for 2 hours
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-278c92154b614240a64c30fafb9f9d86
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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