Hydrochloric Acid → 8-nitro-2-(2-(trifluoromethyl)pyridin-3-yl)-4H-chromen-4-one

HRID 876532Notes

Reaction equation

HRID 876532 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:25])[CH2:12][C:13]([C:15]1[C:16]([C:21]([F:24])([F:23])[F:22])=[N:17][CH:18]=[CH:19][CH:20]=1)=O.Cl>CC(O)=O>[N+:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:2]=1[O:1][C:13]([C:15]1[C:16]([C:21]([F:22])([F:24])[F:23])=[N:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]2=[O:25])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 584772721-(2-Hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)propane-1,3-dione

Product 1

HCID 584773058-nitro-2-(2-(trifluoromethyl)pyridin-3-yl)-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2-hydroxy-3-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)propane-1,3-dione 26 (135 mg, 0.38 mmol), conc. HCl (0.2 ml) and AcOH (5 ml) was stirred at 100° C. for 3.5 h. The reaction mixture was concentrated and sat. aq Na2CO3 was added. The resulting solid was collected by filtration to give 27 as a yellow solid, which was used for the next step without other treatment.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsat. aq Na2CO3 was added
  3. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-ca4cd43bff224b48932e06da8acb9203
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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