Citric Acid → HCID 59864788, compound

HRID 2423272Notes

Reaction equation

HRID 2423272 reaction equation
F[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=1[O:23][CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.O>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=2[O:23][CH3:24])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1738Homovanillic AcidHCID 10796Cesium carbonateHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 59864788HCID 59864788, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-fluoro-3-nitroaniline (3.45 g, 22.1 mmol), 4-hydroxy-3-methoxyphenylacetic acid (4.03 g, 22.1 mmol) and cesium carbonate (18.0 g, 55.3 mmol) in methylsulfoxide (40 mL) was heated to 120° C. (external temperature, oil bath) overnight. After 16 h the reaction was poured into water and the pH adjusted to <4 by addition of citric acid. The aqueous mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with water then brine. The organic separation was stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a dark brown oil. The product was isolated by chromatography on silica gel, eluting with an ethyl acetate/hexane gradient, to afford an orange foamy solid. LC-MS ESI (neg.) m/z: 317.0 (M−H). 1H NMR (400 MHz) (CDCl3) δ 7.27 (d, J=8.4 Hz, 1H); 6.93 (s, 1H); 6.84-6.79 (m, 4H); 5.90 (br s, 2H); 3.85 (s, 31H); 3.63 (s, 2H) ppm.

Workup

  1. extractionThe aqueous mixture was extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water
  3. customThe organic separation
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  6. customto afford a dark brown oil
  7. customThe product was isolated by chromatography on silica gel
  8. washeluting with an ethyl acetate/hexane gradient
  9. customto afford an orange foamy solid

Sources & evidence

ORD record
ord-6ba7161a598c440fb0dc065721fd6c29
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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