Hydrochloric Acid → HCID 67037009, compound

HRID 1401295Notes

Reaction equation

HRID 1401295 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]([C:8]1[C:9]([C:15]([F:18])([F:17])[F:16])=[N+:10]([O-:14])[CH:11]=[CH:12][CH:13]=1)=[O:7])[CH3:2].Br[CH2:21][C:22]([C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[C:27]([O:33][CH3:34])=[C:26]([O:35][CH3:36])[CH:25]=1)=O.Cl>N1C=CC=CC=1>[CH3:36][O:35][C:26]1[CH:25]=[C:24]([C:22]2[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:19])=[C:6]([C:8]3[C:9]([C:15]([F:17])([F:16])[F:18])=[N+:10]([O-:14])[CH:11]=[CH:12][CH:13]=3)[O:7][CH:21]=2)[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[C:27]=1[O:33][CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67036724HCID 67036724, compoundHCID 714457912-Bromo-1-(3,4-dimethoxy-5-nitrophenyl)ethan-1-one

Product 1

HCID 67037009HCID 67037009, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3-(3-ethoxy-3-oxopropanoyl)-2-(trifluoromethyl)pyridine-1-oxide (1.39 g, 5 mmol) in pyridine (25 mL) was added 2-bromo-1-(3,4-dimethoxy-5-nitrophenyl)ethanone (1.67 g, 5.5 mmol). The reaction mixture was heated to 70° C. and stirred for 5 hours, then cooled to room temperature and poured onto 6 N aqueous HCl (100 mL). The precipitate was filtered off, washed with water and dried over P2O5 under vacuum. The solid was recrystallised from dichloromethane/isopropanol to give crude 3-(4-(3,4-dimethoxy-5-nitrophenyl)-3-(ethoxycarbonyl)furan-2-yl)-2-(trifluoromethyl)pyridine 1-oxide, 1.05 g (43%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. dry with materialdried over P2O5 under vacuum
  5. customThe solid was recrystallised from dichloromethane/isopropanol

Sources & evidence

ORD record
ord-98cdad04dc5d479888bde889ebdff250
Source dataset
uspto-grants-2014_12
Patent number
US08907099B2

Reaction notes

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