Sodium Carbonate → HCID 20391045, compound

HRID 426535Notes

Reaction equation

HRID 426535 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[CH:11][C:12]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:13][CH:14]=3)[C:9](=[O:25])[C:8]=2[CH:7]=1.[C:27](=O)([O-])[O-].[Na+].[Na+].CN(N=O)C(=O)OCC>CO.CCOCC.Cl>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][O:19][C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[C:8](=[CH:7][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:26])[CH3:1])=[CH:18][CH:17]=3)[C:9]([OH:25])=[CH:27][C:10]=2[CH:11]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 12001N-Nitroso-N-methylurethaneHCID 3015428HCID 3015428, compound

Product 1

HCID 20391045HCID 20391045, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 8.1 g (0.023 mole) of 2,7-bis[2-(dimethylamino)ethoxy]fluoren-9-one in 50 ml of methanol and 25 ml of ether is stirred and treated with 0.5 gram of finely powdered sodium carbonate. To this mixture is added 75 g (0.06 mole) of ethyl N-methyl-N-nitrosocarbamate in 20 ml of methanol over a period of 2 hours. The temperature of this reaction mixture is kept below 30° C. for a period of 24 hours. The reaction mixture is then freed of most of the volatile materials in vacuo, dissolved in an aqueous solution of hydrochloric acid, and extracted several times with diethyl ether. The resulting aqueous solution is made strongly alkaline with an aqueous sodium hydroxide solution and extracted with ether. The remaining aqueous solution is neutralized to an approximate pH of 10 using a 10% hydrochloric acid solution and extracted with ether. Evaporation of the combined ether extracts in vacuo and recrystallization from a methanol-water mixture yields the desired 2,7-bis[2-(dimethylamino)ethoxy]- 9-phenanthrol.

Workup

  1. extractionextracted several times with diethyl ether
  2. extractionextracted with ether
  3. extractionextracted with ether
  4. customEvaporation of the combined ether
  5. customextracts in vacuo and recrystallization from a methanol-water mixture

Sources & evidence

ORD record
ord-776152c4f41648c0a2e85ad061f382f0
Source dataset
uspto-grants-1979_10
Patent number
US04169897

Reaction notes

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