Hydrochloric Acid → 1H-Isoindole-1,3(2H)-dione, 2-[3-(4-aminophenoxy)propyl]-

HRID 1417334Notes

Reaction equation

HRID 1417334 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]C(=O)C)=[CH:18][CH:17]=1.Cl>C(O)C>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH2:13][CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13453024HCID 13453024, compound

Product 1

HCID 30666931H-Isoindole-1,3(2H)-dione, 2-[3-(4-aminophenoxy)propyl]-Yield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.0 g of N-[4-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propoxy]phenyl]acetamide (Example 94) in 500 ml of ethanol is treated with 100 ml of HCl and refluxed for 8 hours and allowed to stand at room temperature for 18 hours. The precipitate is collected, washed with 50 ml of ethanol and air dried to give 8.6 g of solid as the hydrochloride salt. A 1.5 g sample is crystallized from ethanol: water to give 1.2 g of the HCl salt of the title compound, m.p. 250°-260° C.

Workup

  1. temperaturerefluxed for 8 hours
  2. customThe precipitate is collected
  3. washwashed with 50 ml of ethanol and air
  4. customdried

Sources & evidence

ORD record
ord-c46d427fa1c143d8a7fb3e8259f25cbc
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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