Ethyl Acrylate → HCID 67247001, compound

HRID 1422899Notes

Reaction equation

HRID 1422899 reaction equation
N12CCN(CC1)CC2.[SH:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[CH2:20][OH:21])=[CH:17][C:16]([O:22][CH3:23])=[CH:15][CH:14]=2.[CH2:24]([O:26][C:27](=[O:30])[CH:28]=[CH2:29])[CH3:25]>>[CH2:24]([O:26][C:27]([CH:28]1[CH:20]([OH:21])[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH3:23])[CH:17]=3)[N:12]=[CH:11][C:10]=2[S:9][CH2:29]1)=[O:30])[CH3:25]

Participants

4

Reactant 3

HCID 8821Ethyl AcrylateHCID 9237DabcoHCID 67246941HCID 67246941, compound

Product 1

HCID 67247001HCID 67247001, compoundYield 99.5%

Procedure

1,4-diazabicyclo[2.2.2]octane (1.04 g, 9.26 mmol) is added at room temperature to a stirred solution of (3-mercapto-6-methoxy-quinoline-4-yl)-methanol and its corresponding dimer (2.02 g) in acrylic acid ethyl ester (21.7 mL, 203.72 mmol). The reaction mixture is heated under reflux for 2 hours, cooled down to room temperature and concentrated to afford 4-hydroxy-6-methoxy-3,4-dihydro-2H-1-thia-9-aza-phenanthrene-3-carboxylic acid ethyl ester as a dark brown solid (1.47 g, 99.5% yield).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3fdc22ff49b5434ebfd4a2c9096bd2ab
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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