4-Aminophenol → HCID 178435504, compound

HRID 1457502Notes

Reaction equation

HRID 1457502 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-:9].[K+].Br[CH2:12][CH2:13][CH2:14][C:15]1[C:35]2[NH:36][C:17](=[CH:18][C:19]3[C:20]([CH2:48][CH3:49])=[C:21]([CH3:47])[C:22]([N:46]=3)=[CH:23][C:24]3[NH:28][C:27]([CH:29]=[C:30]4[N:37]=[C:33]([CH:34]=2)[C:32]([CH2:38][CH2:39][CH2:40]Br)=[C:31]4[CH3:42])=[C:26]([CH3:43])[C:25]=3[CH2:44][CH3:45])[C:16]=1[CH3:50]>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:13][CH2:14][C:15]2[C:35]3[NH:36][C:17](=[CH:18][C:19]4[C:20]([CH2:48][CH3:49])=[C:21]([CH3:47])[C:22]([N:46]=4)=[CH:23][C:24]4[NH:28][C:27]([CH:29]=[C:30]5[N:37]=[C:33]([CH:34]=3)[C:32]([CH2:38][CH2:39][CH2:40][O:9][C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=3)=[C:31]5[CH3:42])=[C:26]([CH3:43])[C:25]=4[CH2:44][CH3:45])[C:16]=2[CH3:50])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 14797Potassium HydroxideHCID 178435501HCID 178435501, compound

Product 1

HCID 178435504HCID 178435504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.28 g (30.10 mmol) of 4-aminophenol and 1.69 g (30.10 mmol) of powdered potassium hydroxide are stirred in 50 ml of anhydrous dimethylformamide under argon for 30 minutes at room temperature and then mixed with 2.00 g (3.01 mmol) of 13,17-bis-(3-bromopropyl)-3,8-diethyl-2,7,12,18-tetramethylporphyrin (CA RN 112635-99-1). After 30 hours of stirring at room temperature, it is filtered, substantially concentrated by evaporation in a vacuum, the residue is taken up in methylene chloride and shaken out once each with water and with saturated aqueous sodium bicarbonate solution. The organic phase is dried on sodium sulfate, filtered and concentrated by evaporation and the residue is chromatographed to aluminum oxide with methylene chloride/methanol. After the concentration by evaporation, the product is obtained as reddish brown solid, which can be recrystallized from methylene chloride/ether.

Workup

  1. filtrationit is filtered
  2. concentrationsubstantially concentrated by evaporation in a vacuum
  3. stirringshaken out once each with water
  4. customThe organic phase is dried on sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customthe residue is chromatographed to aluminum oxide with methylene chloride/methanol
  8. concentrationAfter the concentration
  9. customby evaporation
  10. customthe product is obtained as reddish brown solid, which
  11. customcan be recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-8a455bd856e14eaa8a50fd4df361f2f0
Source dataset
uspto-grants-1998_12
Patent number
US05849259

Reaction notes

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