Hydrochloric Acid → N-(7-chloro-2,3-dihydro-2-methyl-1H-isoindol-4-yl)acetamide

HRID 48216Notes

Reaction equation

HRID 48216 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:11][C:12](=[O:14])[CH3:13])[CH2:3]1.Cl.[Cl:16]([O-])=O.[Na+]>C(O)C>[Cl:16][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:9]2[C:4]=1[CH2:3][N:2]([CH3:1])[CH2:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22742473HCID 22742473, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 22742484N-(7-chloro-2,3-dihydro-2-methyl-1H-isoindol-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(2,3-dihydro-2-methyl-1H-isoindol-4-yl)acetamide (20 g), hydrochloric acid (37%, 2.5 mL), and sodium chlorite (15%, 10 ml) in 96% ethanol (20 mL) was stirred at room temperature for 4 hours. The solvent was removed by evaporation, whereafter the residue was treated with saturated Na2CO3 in water to pH=7. The precipitated product was filtered off and washed with water and ether. Yield 1.1 g, mp 147-150° C.

Workup

  1. customThe solvent was removed by evaporation, whereafter the residue
  2. additionwas treated with saturated Na2CO3 in water to pH=7
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water and ether

Sources & evidence

ORD record
ord-fbf0c72f953f40b19e16a5b5052f034b
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

Loading…