2-Aminophenol → HCID 10467044, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C[O:10][C:11](OC)(OC)[C:12](OC)=O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[CH3:45][N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1.OC1C=CC=CN=1>C1(C)C=CC=CC=1>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:12]1[C:11]([N:49]1[CH2:50][CH2:51][N:46]([CH3:45])[CH2:47][CH2:48]1)=[O:10]Participants
Conditions
- Temperature
- 125 °C
Procedure
A stirred solution of 2-aminophenol (300 mg, 2.75 mmol), methyl 2,2,2-trimethoxyacetate (902 mg, 5.50 mmol), and ytterbium triflate (170 mg, 0.28 mmol) in toluene (10 mL) was heated to reflux. After 5 h, the mixture was cooled, and the precipitate was collected and dried. The crude solid was suspended in toluene (5 mL), and N-methylpiperazine (1.5 mL, 13.7 mmol) was added followed by 2-hydroxypyridine (26 mg, 0.28 mmol). The mixture was heated to 125° C. in a sealed tube for 4 h. The resulting yellow solution was concentrated under reduced pressure, and the residue was purified on silica gel (12 g; 2% methanol/dichloromethane), yielding 320 mg (48%) of the title compound. MS (ESI): mass calculated for C13H15N3O2, 245.12; m/z found, 246.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.83-7.79 (m, 1H), 7.66-7.65 (m, 2H), 7.47-7.41 (m, 2H), 4.19 (t, J=5.1 Hz, 4H), 3.88 (t, J=5.1 Hz, 4H), 2.55-2.52 (m, 4H), 2.35 (s, 3H). 13C NMR (400 MHz, CDCl3): 156.1, 154.6, 149.9, 140.1, 127.1, 125.3, 121.3, 111.5, 55.3, 54.6, 46.9, 45.9, 42.8.
Workup
- temperaturethe mixture was cooled
- customthe precipitate was collected
- customdried
- concentrationThe resulting yellow solution was concentrated under reduced pressure
- customthe residue was purified on silica gel (12 g; 2% methanol/dichloromethane)
Sources & evidence
- ORD record
- ord-d98907bde2ad45d1b0f8b22747e034d8
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504426B2
Reaction notes
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