3-Nitrophenol → HCID 2966316, compound

HRID 1980741Notes

Reaction equation

HRID 1980741 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 2966316HCID 2966316, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A partial suspension of m-nitrophenol (6.0 g; 43.0 mmoles), N-(3-bromopropyl)phthalimide (10.0 g; 37.0 mmoles) and potassium carbonate (8.0 g; 58.0 mmoles) in 50 ml of DMF was stirred at ambient temperature for 70 hours. The reaction mixture was diluted with 80 ml of water and filtered to give product. Recrystallization from 2-methoxyethanol yielded 9.15 g of the title compound, mp 149°-152°.

Workup

  1. filtrationfiltered
  2. customto give product
  3. customRecrystallization from 2-methoxyethanol

Sources & evidence

ORD record
ord-885718f09069471db8a7efac11dc7230
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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