Guanidine Hydrochloride → HCID 178509681, compound

HRID 479567Notes

Reaction equation

HRID 479567 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CC([O-])(C)C.[K+].Cl[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=3)[CH:21]=2)[C:16]([Cl:31])=[CH:15][N:14]=1>COCCOC.CN1C(=O)CCC1>[Cl:31][C:16]1[C:17]2[C:22](=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=3)=[CH:19][CH:18]=2)[C:13]([NH:4][C:3]([NH2:5])=[NH:2])=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 187712921,4-Dichloro-7-(3-cyanophenyl)isoquinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 178509681HCID 178509681, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred suspension of guanidine hydrochloride (3.8 kg, 39.8 mol) and KOtBu (4.28 kg, 38.1 mol) in DME (17.6 L) was heated to reflux under N2 for 1 hour. The gum containing solution was cooled to room temperature, diluted with NMP (8.8 L) and 1,4-dichloro-7-(3-cyanophenyl)isoquinoline (4.4 kg, 14.7 mol) was added as a solid. The mixture was heated at reflux overnight, cooled to room temperature, filtered through a pad of celite and the pad washed with DME (4.4 L). Water (35.2 L) was added to the filtrate. The resultant slurry was stirred for 2 hour and the solid collected by filtration. The solid was washed with water (4.4 L) and dried in vacuo at 50° C. to give (4-chloro-7-(3-cyanophenyl)isoquinolin-1-yl)guanidine (4.55 kg, 14.1 mol, 96%) as a green solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 1 hour
  3. additionThe gum containing solution
  4. additionwas added as a solid
  5. temperatureThe mixture was heated
  6. temperatureat reflux overnight
  7. temperaturecooled to room temperature
  8. filtrationfiltered through a pad of celite
  9. washthe pad washed with DME (4.4 L)
  10. additionWater (35.2 L) was added to the filtrate
  11. filtrationthe solid collected by filtration
  12. washThe solid was washed with water (4.4 L)
  13. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-dfe2bf11a1c6481c80cd8b2502c20e5d
Source dataset
uspto-grants-2003_11
Patent number
US06645979B2

Reaction notes

Loading…