Hydrochloric Acid → HCID 58124938, compound

HRID 1971752Notes

Reaction equation

HRID 1971752 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:16][C:17]([N:19]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:20][CH2:21][C:22]([CH3:27])([CH3:26])[CH2:23][C:24]#[CH:25])=[O:18])[CH:9]2[CH2:12][O:13]CC)=[CH:4][C:3]=1[O:32][CH3:33].[OH-].[K+].[O:36]1CCOCC1.Cl>O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:16][C:17]([N:19]([C:28]([CH3:30])([CH3:31])[CH3:29])[CH2:20][CH2:21][C:22]([CH3:27])([CH3:26])[CH2:23][C:24]#[CH:25])=[O:18])[CH:9]2[C:12]([OH:36])=[O:13])=[CH:4][C:3]=1[O:32][CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 58124836HCID 58124836, compound

Product 1

HCID 58124938HCID 58124938, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 430 mg of 24f, 300 mg of KOH, 10 ml of dioxane and 1.5 ml of water was warmed at 60° C. for 1 hr. Reaction was cooled and diluted with 30 ml of water and acidified to pH3 with 0.5 N HCl. The product was extracted into ethyl acetate. The organic extract was washed twice with water, dried and concentrated, to leave 390 mg of 24g, as a colorless oil. Rf (toluene/acetone 1/1) 0.55. NMR (CDCl3) δ 7.70 and 6.65 (2×s, 2, Ar—H), 5.79 (s, 1, CH), 3.90 (s, 3, OCH3), 1.97 (t, 1, acetylene), 0.90 (s, 6, 2×CH3), 1.55 (s, 9, tertC4H9).

Workup

  1. customReaction
  2. temperaturewas cooled
  3. extractionThe product was extracted into ethyl acetate
  4. extractionThe organic extract
  5. washwas washed twice with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-79b15464b24f4050aed34943294b3ab2
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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