4-Nitrophenol → HCID 18186465, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]1([CH3:22])[CH2:21][O:20]1.[CH:23]([NH2:26])([CH3:25])[CH3:24]>CN(C=O)C>[OH:20][C:19]([CH3:22])([CH2:21][NH:26][CH:23]([CH3:25])[CH3:24])[CH2:18][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 4-nitrophenol (1.0 g, 7.1 mmol), potassium carbonate (1.30 g, 9.4 mmol) and 2-chloromethyl-2-methyloxirane (0.84 g, 7.9 mmol) in DMF (50 ml) was stirred for 12 hours and then heated at 80° C. for 12 hours. Insoluble material was removed by filtration and washed with DMF (10 ml). The combined filtrate and washings were concentrated and the residue was dissolved in methanol (20 ml). Isopropylamine (6.13 ml, 71 mmol) was added and the mixture was stirred for 12 hours. Volatile material was removed by evaporation and the residue was purified by bond elute chromatography, eluting with 0-5% methanol in DCM, to give the product as a yellow solid (0.5 g, 26%). MS (MH+): 269.
Workup
- customInsoluble material was removed by filtration
- washwashed with DMF (10 ml)
- concentrationThe combined filtrate and washings were concentrated
- dissolutionthe residue was dissolved in methanol (20 ml)
- stirringthe mixture was stirred for 12 hours
- customVolatile material was removed by evaporation
- customthe residue was purified by bond
- washelute chromatography
- washeluting with 0-5% methanol in DCM
Sources & evidence
- ORD record
- ord-924929360ca645629b38347949e55775
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06593326B1
Reaction notes
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