Ammonia → HCID 60132550, compound

HRID 1591525Notes

Reaction equation

HRID 1591525 reaction equation
[N:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][N:12]=3)[C:7](=O)[C:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:17]1[C:30]2[C:21](=[CH:22][C:23]3[C:28]([C:29]=2[CH:31]=O)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:19][CH:18]=1.C([O-])(=O)C.[NH4+:37].[NH3:38]>C(O)(=O)C.O>[CH:17]1[C:30]2[C:21](=[CH:22][C:23]3[C:28]([C:29]=2[C:31]2[NH:37][C:7]4[C:6]([N:38]=2)=[C:5]2[C:14](=[C:13]5[C:8]=4[CH:9]=[CH:10][CH:11]=[N:12]5)[N:1]=[CH:2][CH:3]=[CH:4]2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 695049-AnthracenecarboxaldehydeHCID 728101,10-Phenanthroline-5,6-dioneHCID 517165Ammonium Acetate

Product 1

HCID 60132550HCID 60132550, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 1,10-phenanthroline-5,6-dione (10 grams, purchased from Aldrich Co.), 9-anthraldehyde (14.7 grams) and ammonium acetate (51.4 grams) was placed into a round bottom flask and dissolved in 200 milliliters of glacial acetic acid. The solution was heated under reflux for 4 hours at which time the reaction was cooled to room temperature and diluted with water. The solution was neutralized with concentrated aqueous ammonia and the precipitate was collected by filtration and washed with water and then dichloromethane and dried to give 17 grams of 2-(9-anthryl)imidazo[4,5-f]-[1,10]phenanthroline. The product and its structure was confirmed by proton NMR analysis.

Workup

  1. customwas placed into a round bottom flask
  2. temperatureThe solution was heated
  3. temperatureunder reflux for 4 hours at which time the reaction
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. dry with materialdichloromethane and dried

Sources & evidence

ORD record
ord-a0288ceb8a0b403db43000114891de65
Source dataset
uspto-grants-2007_11
Patent number
US07291404B2

Reaction notes

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