Hydrochloric Acid → 1-(2-Hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)propane-1,3-dione

HRID 876531Notes

Reaction equation

HRID 876531 reaction equation
C1CCN2C(=NCCC2)CC1.[OH:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[C:22](=[O:24])[CH3:23].[F:25][C:26]([F:37])([F:36])[C:27]1[C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=[CH:29][N:28]=1.Cl>N1C=CC=CC=1>[OH:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[C:22](=[O:24])[CH2:23][C:33]([C:32]1[C:27]([C:26]([F:37])([F:25])[F:36])=[N:28][CH:29]=[CH:30][CH:31]=1)=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2700261-(2-Hydroxy-3-nitrophenyl)-ethanoneHCID 450819512-(Trifluoromethyl)nicotinoyl chloride

Product 1

HCID 584772721-(2-Hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)propane-1,3-dioneYield 38.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

DBU (334 mg, 2.2 mmol) was added to a solution of 1-(2-Hydroxy-3-nitrophenyl)ethanone 1 (181 mg, 1 mmol) and 2-(trifluoromethyl)pyridine-3-carbonyl chloride 25 (1.1 mmol) in pyridine (3 ml). The mixture was stirred at 70° C. for 12 h, poured into 2N HCl (20 ml) and extracted with EtOAc. The organic layers were dried over Na2SO4, concentrated and purified by preparative TLC (CH2Cl2/EtOAc, 10:1) to give 26 as a yellow solid (135 mg, 38% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by preparative TLC (CH2Cl2/EtOAc, 10:1)

Sources & evidence

ORD record
ord-8d12561489ed4d96aee1642e0e99487e
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

Loading…