Methanol → HCID 10088255, compound

HRID 1647457Notes

Reaction equation

HRID 1647457 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[C:11](CC(=O)C1C=CC=CC=1)[CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH-:33].[Na+].[CH3:35]O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[C:11]([CH2:35][OH:33])[CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19923017HCID 19923017, compound

Product 1

HCID 10088255HCID 10088255, compound

Procedure

To a stirring suspension of 3-butyryl-4-(2-methyl-phenylamino)-7-benzoylmethylquinoline (2.74 g, 6.25 mmol) in methanol (25 ml) was added 2N sodium hydroxide (6.24 ml). Stirring was continued for 18 hours, then the solvent evaporated in vacuo and the residue treated with water and extracted with chloroform. The combined extracts were dried (Na2SO4) and evaporated to a solid, which was purified by column chromatography (silica, chloroform-methanol) to give the title compound (1.31 g), m.p. 176°-8°, from methanol.

Workup

  1. customthe solvent evaporated in vacuo
  2. additionthe residue treated with water
  3. extractionextracted with chloroform
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated to a solid, which
  6. customwas purified by column chromatography (silica, chloroform-methanol)

Sources & evidence

ORD record
ord-63670b3bf2254126b5ccd8794b857021
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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