Water → HCID 59730077, compound

HRID 228172Notes

Reaction equation

HRID 228172 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10393TyrosolHCID 11430Potassium CarbonateHCID 804566-Chloronicotinamide

Product 1

HCID 59730077HCID 59730077, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Combine 4-(2-hydroxy-ethyl)-phenol (2.0 g, 14.5 mmol), 6-chloronicotinamide (2.3 g, 14.5 mmol) and K2CO3 (5.0 g, 36.2 mmol) in DMF (40 mL) under nitrogen, stir and heat at 120° C. overnight. Cool to ambient temperature and pour into water, extract the aqueous layer with ethyl acetate. Combine the organic layers and dry over Na2SO4. Eliminate the solvent and purify by flash chromatography on silica gel (eluent: CHCl3/7% EtOH/0.7% NH4OH) to give the title compound (1.8 g, 49%). Electrospray MS M+1 ion=259, 1H-NMR (DMSO-d6, 400 MHz): 8.58 (d, 1H, J=2.7 Hz), 8.22 (dd, 1H, J=2.7 and 8.8 Hz), 8.00 (bs, 1H), 7.46 (bs, 1H), 7.25 (m, 2H), 7.05-7.02 (m, 3H), 4.65 (t, 1H, J=5.3 Hz), 3.63-3.58 (m, 2H), 2.72 (t, 2H, J=6.9 Hz).

Workup

  1. temperatureCool to ambient temperature
  2. extractionextract the aqueous layer with ethyl acetate
  3. dry with materialdry over Na2SO4
  4. custompurify by flash chromatography on silica gel (eluent: CHCl3/7% EtOH/0.7% NH4OH)

Sources & evidence

ORD record
ord-77fe6f2f3f184e56a84f8b2aebd7c7f6
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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