Phenol → HCID 85997670, compound

HRID 2252246Notes

Reaction equation

HRID 2252246 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[C:11]1(O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CCOCC>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 792226-Chloronicotinic acid

Product 1

HCID 85997670HCID 85997670, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 6-chloronicotinic acid (68.0 g, 0.431 mol), phenol (40.6 g, 0.431 mol), DCC (93.6 g, 0.453 mol), and DMAP (1.60 g, 0.0129 mol) in ether (1 L) was stirred at room temperature overnight. The solvent was evaporated and the residue was stirred in CH2Cl2. The solid was filtered and the filtrate was purified by flash chromatography eluted with CH2Cl2 to give 88.0 g (88%) of the desired product. MS (DCI/NH3) m/z: 234.0 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 7.22 (d, J=8.14 Hz, 2H) 7.31 (t, J=7.29 Hz, 1H) 7.47 (dd, J=17.12, 7.97 Hz, 3H) 8.40 (m, 1H) 9.17 (d, J=1.70 Hz, 1H).

Workup

  1. customThe solvent was evaporated
  2. stirringthe residue was stirred in CH2Cl2
  3. filtrationThe solid was filtered
  4. customthe filtrate was purified by flash chromatography
  5. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-08cbb5ae90c84533b5d5e16e306b56e5
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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