Methane → Quinoline-5-carboxylic acid

HRID 400188Notes

Reaction equation

HRID 400188 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[N+]([C:14]1[CH:15]=C(S([O-])(=O)=O)C=C[CH:19]=1)([O-])=O.OCC(CO)O.S(=O)(=O)(O)O.[OH-].[NH4+].C>O.C(O)(=O)C>[N:1]1[C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=2[CH:15]=[CH:14][CH:19]=1

Participants

9

Reactant 6

HCID 297MethaneHCID 753GlycerolHCID 1118Sulfuric AcidHCID 74193-Aminobenzoic AcidHCID 14923Ammonium HydroxideHCID 390696130904-40-6

Product 1

HCID 232489Quinoline-5-carboxylic acidYield 35.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution containing 15 g (0.1 mol) of m-aminobenzoic acid, 27 g (0.13 mol) of m-nitrobenzene sulfonate and 25 g (0.4 mol) of glycerol, was added 125 g of 70% sulfuric acid. The resultant reaction mixture was refluxed for about 2.5 hours, diluted with 125 mL of water, basified to pH 9 using ammonium hydroxide, stirred overnight with 5 g of charcoal, and then filtered. The filtrate was then boiled with 5 g charcoal, filtered, and then cooled to 50° C., acidified to pH 5 with glacial acetic acid (15 mL), and filtered to provide a brown solid. This solid was boiled in 300 mL of water containing 10 mL of acetic acid and hot filtered to provide crude material. This material was purified using recrystallization from boiling acetic acid to provide 6.1 g of a pale brown solid. Yield: 32%.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas refluxed for about 2.5 hours
  3. filtrationfiltered
  4. filtrationfiltered
  5. filtrationfiltered
  6. customto provide a brown solid
  7. filtrationhot filtered
  8. customto provide crude material
  9. customThis material was purified
  10. customrecrystallization

Sources & evidence

ORD record
ord-2eb4b39d75b54022847373d083c6e2c2
Source dataset
uspto-grants-1998_10
Patent number
US05827859

Reaction notes

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