Methanol → 8-Methoxy-2-propyl-5-quinolinecarboxylic acid

HRID 392212Notes

Reaction equation

HRID 392212 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([CH2:13][CH2:14][CH3:15])[CH:9]=[CH:8][C:7]=2[C:6]([C:16]([O:18]C)=[O:17])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].CO>O>[CH3:1][O:2][C:3]1[C:12]2[N:11]=[C:10]([CH2:13][CH2:14][CH3:15])[CH:9]=[CH:8][C:7]=2[C:6]([C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 22663351HCID 22663351, compound

Product 1

HCID 226632518-Methoxy-2-propyl-5-quinolinecarboxylic acidYield 45.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 8-methoxy-2-n-propylquinoline-5-carboxylate (1.0g, Reference Example 27), potassium carbonate (0.8 g), methanol (30 ml), and water (2 ml was refluxed for 5 hours. The solution was concentrated, then diluted with water and then washed with diethyl ether. The pH of the aqueous phase was adjusted to 6 by addition of hydrochloric acid (6M). The resulting cream precipitate was washed with water and then dried at 60° C. to give the title compound (0.43 g) as a cream coloured solid, m.p. 214-217° C. [Elemental analysis:— C, 67.00; H, 6.32; N, 5.53%. Calculated for C14H15NO3.0.25H2O:— C, 67.30; H, 6.06; N, 5.61%].

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe solution was concentrated
  3. additiondiluted with water
  4. washwashed with diethyl ether
  5. additionThe pH of the aqueous phase was adjusted to 6 by addition of hydrochloric acid (6M)
  6. washThe resulting cream precipitate was washed with water
  7. customdried at 60° C.

Sources & evidence

ORD record
ord-3391f6572b5a4b98889d8e99e6e67d1a
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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