Toluene → 6-Methoxy-2-methoxycarbonylquinoline

HRID 1684538Notes

Reaction equation

HRID 1684538 reaction equation
S(Cl)(Cl)=O.[C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[N:9]=1)([OH:7])=[O:6].[C:20]1(C)C=CC=CC=1>CO.C(OCC)C.C(OCC)(=O)C>[CH3:19][O:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:5]([O:7][CH3:20])=[O:6])[CH:17]=[CH:16]2

Participants

7

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 111832986-methoxyquinoline-2-carboxylic Acid

Product 1

HCID 190398666-Methoxy-2-methoxycarbonylquinoline

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

230 ml (3.17 mol) of thionyl chloride are run dropwise onto a suspension of 129 g (0.635 mol) of 2-carboxy-6-methoxyquinoline in 1200 ml of toluene, and the mixture is heated for 3 h 30 min. After concentrating the solution under reduced pressure, the solid obtained is dissolved in 300 ml of methanol. The mixture is stirred for 30 min, the solvent is then evaporated off under reduced pressure, and the product obtained is taken up in diethyl ether and isolated by filtration. The solid obtained is taken up in ethyl acetate and dilute aqueous ammonia, and the organic phase is then separated out, treated with animal black, filtered and concentrated under reduced pressure. 90 g of product are thus obtained.

Workup

  1. temperaturethe mixture is heated for 3 h 30 min
  2. concentrationAfter concentrating the solution under reduced pressure
  3. customthe solid obtained
  4. customthe solvent is then evaporated off under reduced pressure
  5. customthe product obtained
  6. customisolated by filtration
  7. customThe solid obtained
  8. customdilute aqueous ammonia, and the organic phase is then separated out
  9. additiontreated with animal black,
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d21b8506f2ca4c40b481c9c43f94118e
Source dataset
uspto-grants-1997_06
Patent number
US05641785

Reaction notes

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