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Potassium Carbonate → 2,7,7-Trimethyl-5-(2-diethylamino-ethyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione hydrochloride

HRID 47112
Notes
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Reaction equation

HRID 47112 reaction equation
[CH3:1][C:2]1[N:18]=[C:5]2[C:6](=[O:17])[CH2:7][CH:8]3[C:13]([CH:12]=[N:11][C:10]([CH3:15])([CH3:14])[C:9]3=[O:16])=[C:4]2[N:3]=1.Cl.[CH2:20]([N:22]([CH2:25][CH2:26][Cl:27])[CH2:23][CH3:24])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[ClH:27].[CH3:1][C:2]1[N:18]=[C:5]2[C:6](=[O:17])[CH:7]([CH2:21][CH2:20][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:8]3[C:13]([CH:12]=[N:11][C:10]([CH3:14])([CH3:15])[C:9]3=[O:16])=[C:4]2[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 706107882,7,7-trimethyl-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione

Product 1

HCID 706111972,7,7-Trimethyl-5-(2-diethylamino-ethyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

4.2 gm of 2,7,7-trimethyl-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione were dissolved in 100 ml of dimethylformamide, and the solution was admixed with 3.4 gm of diethylamino ethyl chloride hydrochloride and 4.1 gm of potassium carbonate. The mixture was refluxed for 8 hours, the solvent was distilled off in vacuo, the residue was admixed with water and extracted with chloroform. The chloroform phase was evaporated and the residue was purified on a silicagel column (eluant: chloroform/acetone 19:1). The dihydrochloride was precipitated from acetone/methanol with ethereal hydrochloric acid and recrystallized from acetone/methanol.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. distillationthe solvent was distilled off in vacuo
  3. extractionextracted with chloroform
  4. customThe chloroform phase was evaporated
  5. customthe residue was purified on a silicagel column (eluant: chloroform/acetone 19:1)
  6. customThe dihydrochloride was precipitated from acetone/methanol with ethereal hydrochloric acid
  7. customrecrystallized from acetone/methanol

Sources & evidence

ORD record
ord-866b4918b68a46828ad29f644d56bd5a
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04176184

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes