2-Bromoethanol → HCID 10247304, compound

HRID 1647490Notes

Reaction equation

HRID 1647490 reaction equation
[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[CH:12][CH:11]=[CH:10][C:9]=2[OH:23])(=[O:4])[CH2:2][CH3:3].[CH3:24][C:25](C)([O-:27])C.[K+].BrCCO>COCCOCCOC>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[CH:12][CH:11]=[CH:10][C:9]=2[O:23][CH2:24][CH2:25][OH:27])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 108982-Bromoethanol2×HCID 10357805HCID 10357805, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10247304HCID 10247304, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

A solution of 3-propanoyl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.06 g, 10 mmol) and potassium t-butoxide (1.68 g, 15 mmol) in diglyme (50 ml) was heated to 150°, a solution of 2-bromoethanol (0.85 ml, 12 mmol) in diglyme (25 ml) added dropwise, then the mixture raised to reflux temperature with vigorous stirring. After 1 hour a further portion of 2-bromoethanol (0.85 ml) was added, and reflux continued for 2 hours. The diglyme was evaporated, the residue taken up in dichloromethane, washed with water and brine, dried and evaporated. Chromatography (silica gel, ethyl acetate/2% acetic acid/2-5% methanol) and recrystallisation from aqueous isobutyl alcohol gave 3-propanoyl-4-(2-methylphenylamino)-8-(2-hydroxyethoxy)-quinoline (0.48 g), m.p. 174°-176°.

Workup

  1. temperaturethe mixture raised
  2. temperatureto reflux temperature with vigorous stirring
  3. temperaturereflux
  4. customThe diglyme was evaporated
  5. washwashed with water and brine
  6. customdried
  7. customevaporated
  8. customChromatography (silica gel, ethyl acetate/2% acetic acid/2-5% methanol) and recrystallisation from aqueous isobutyl alcohol

Sources & evidence

ORD record
ord-f2e669946c4340ff80630bd225a15b68
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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