Acetone → HCID 178439760, compound

HRID 1088938Notes

Reaction equation

HRID 1088938 reaction equation
N.[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[CH:16]=[C:15]4[NH:17][C:18](=[O:20])[CH2:19][C:14]4=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.C(O)C.[CH3:24][C:25]([CH3:27])=O>O>[C:25](=[C:19]1[C:14]2[C:15](=[CH:16][C:10]3[NH:9][C:8]([C:5]4[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=4)=[N:12][C:11]=3[CH:13]=2)[NH:17][C:18]1=[O:20])([CH3:27])[CH3:24]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 222AmmoniaHCID 702EthanolHCID 178515303HCID 178515303, compound

Product 1

HCID 178439760HCID 178439760, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ammonia is passed up to saturation into a suspension of 0.4 g. (1.6 mmol) 2-(4-pyridyl)-6,7-dihydro-3H,5H-pyrrolo[2,3-f]benzimidazol-6-one in 20 ml. ethanol and 10 ml. acetone and the reaction mixture then stirred for 2 hours at 60° C. Subsequently, a further 10 ml. acetone are added thereto and stirring continued for 4 hours at 60° C., whereafter the reaction mixture is evaporated, the residue is taken up in ethanol, acidified and suction filtered from the precipitate. The residue obtained is dissolved in water and rendered neutral and the crystals obtained are filtered off with suction and recrystallised from isopropanol/ethyl acetate. Yield: 40 mg. (9% of theory); m.p. >300° C.

Workup

  1. customis evaporated
  2. filtrationsuction filtered from the precipitate
  3. customThe residue obtained
  4. customthe crystals obtained
  5. filtrationare filtered off with suction
  6. customrecrystallised from isopropanol/ethyl acetate

Sources & evidence

ORD record
ord-5eac657386664cdd88e85762f66a19ed
Source dataset
uspto-grants-1990_10
Patent number
US04963686

Reaction notes

Loading…