Benzene → HCID 178498115, compound

HRID 1655602Notes

Reaction equation

HRID 1655602 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:11]1C=CC=CC=1.S(=O)(=O)(O)O>CO>[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:11])=[O:5]

Participants

5

Reactant 3

HCID 241BenzeneHCID 1118Sulfuric AcidHCID 178418543HCID 178418543, compound

Product 1

HCID 178498115HCID 178498115, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Hydroxynicotinic acid (6.95 g, 50 mmol) was dissolved in 125 mL of methanol, 75 mL of benzene, and 0.75 mL of concentrated sulfuric acid under nitrogen and heated at reflux for 2.5 hours. A Dean-Stark trap was added to the apparatus and heating was continued overnight. The volatiles were removed under reduced pressure and the resulting solid was suspended in cold water (150 mL) and filtered to remove unreacted starting material. The filtrate was extracted with methylene chloride and chloroform. The combined organic extracts were concentrated in vacuo to afford 2.5 g. Recrystallization from hot benzene afforded 1.7 g (22%) of the title compound. 1H NMR (CD3OD, 300 MHz) δ 3.83 (s, 3H), 6.45 (t, 1H), 7.68 (dd, 1H), 8.29 (dd, 1H). MS (DCl/NH3) m/e 154 (M+H)+.

Workup

  1. temperatureat reflux for 2.5 hours
  2. additionA Dean-Stark trap was added to the apparatus
  3. temperatureheating
  4. customThe volatiles were removed under reduced pressure
  5. filtrationfiltered
  6. customto remove unreacted
  7. extractionThe filtrate was extracted with methylene chloride and chloroform
  8. concentrationThe combined organic extracts were concentrated in vacuo
  9. customto afford 2.5 g
  10. customRecrystallization from hot benzene

Sources & evidence

ORD record
ord-5d334321880c4d13b473b2a61487357e
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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