4-Aminophenol → HCID 57974605, compound

HRID 1864662Notes

Reaction equation

HRID 1864662 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[N:11]([CH3:17])[C:12](=[O:16])[O:13][CH2:14][CH3:15].[OH:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>>[NH2:23][C:22]1[CH:24]=[CH:25][C:19]([O:18][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=2[N:11]([CH3:17])[C:12](=[O:16])[O:13][CH2:14][CH3:15])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 4034-AminophenolHCID 57974577HCID 57974577, compound

Product 1

HCID 57974605HCID 57974605, compoundYield 12%

Procedure

Method A was used with ethyl 4-chloro-2-nitropyridin-3-yl-methyl-carbamate (400 mg, 1.5 mmol) and 4-hydroxyaniline (196 mg, 1.8 mmol) to afford the title compound (56 mg, 12%) after purification by column chromatography, eluent gradient DCM to DCM:AcOEt 1:1. 1H-NMR (δ, ppm, DMSO-d6): 1.06+1.23 (t+t, rotamers, 3H, CH3,Et), 3.18+3.23 (s+s, rotamers, 3H, NCH3), 4.04+4.12 (q+q, rotamers, 2H, CH2,Et), 5.44 (s, 2H, NH2,Ph), 5.97 (s, 2H, NH2,Py2), 6.92 (d, 2H, Harom,Ph,3+5, J=8.79 Hz), 6.92 (d, 2H, Harom,Ph,2+6, J=8.82 Hz), 7.04 (d, 1H, HPy,5, J=5.60 Hz), 8.33 (d, 1H, HPy,6, J=5.59 Hz). LC-MS (m/z): 332 (M+, 100).

Sources & evidence

ORD record
ord-85dd1848ce784d0a888b2647d75e5931
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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