HCID 3088056, compound → 4-Amino-3-{2-[2-(ethylamino)ethyl]-3-oxo-2,3-dihydro-1H-isoindol-1-yl}benzonitrile--hydrogen chloride (1/2)

HRID 231866Notes

Reaction equation

HRID 231866 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]1[CH2:20][CH2:21][NH:22][CH2:23][CH3:24].[ClH:25].C(O)C>C(O)(C)C>[ClH:25].[ClH:25].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][C:3]=1[CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]1[CH2:20][CH2:21][NH:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 3088056HCID 3088056, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 30880554-Amino-3-{2-[2-(ethylamino)ethyl]-3-oxo-2,3-dihydro-1H-isoindol-1-yl}benzonitrile--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The same procedures as in Example 29 were repeated except for using 20 g of 2-cyano-11-hydroxy-5, 11-dihydro-6H-dibenz[b,e]azepin-6-one and 42 ml of N-ethylethylenediamine as the starting materials. Thus, 3-(2-amino-5-cyanophenyl)-2-(2-ethylaminoethyl)isoindolin-1-one (Compound 38) was obtained. After dissolving it in isopropanol, Compound 38 was treated with hydrogen chloride-ethanol solution and the solution was concentrated to dryness under reduced pressure. The obtained solid was crystallized from acetonitrile to give 2.3 g of 3-(2-amino-5-cyanophenyl)-2-(2-ethylaminoethyl)isoindolin-1-one dihydrochloride (Compound 38').

Workup

  1. concentrationthe solution was concentrated to dryness under reduced pressure
  2. customThe obtained solid was crystallized from acetonitrile

Sources & evidence

ORD record
ord-b5b51ce79ac44c33b748cb7049cd5ac1
Source dataset
uspto-grants-1989_07
Patent number
US04849441

Reaction notes

Loading…