Ethanol → HCID 15134190, compound

HRID 718690Notes

Reaction equation

HRID 718690 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.OS(O)(=O)=O.[CH3:20][CH2:21]O>C(Cl)Cl>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([O:14][CH2:20][CH3:21])=[O:13])=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 3199762-Methyl-5-quinolinecarboxylic acid

Product 1

HCID 15134190HCID 15134190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of compound 73a (3.1 g, 16 mmol) in EtOH (50 mL) was added concentrated H2SO4 (1.0 mL) and the resultant slurry was refluxed overnight. The homogeneous solution was cooled, diluted with DCM (300 mL), washed with 1N NaOH (1×100 mL), dried (Na2SO4), and concentrated in vacuo to give compound 73b as an off-white solid. Mass spectrum (LCMS, ESI pos.) Calcd. For C13H13NO2: 216.2 (M+H). found 216.2.

Workup

  1. temperaturethe resultant slurry was refluxed overnight
  2. temperatureThe homogeneous solution was cooled
  3. washwashed with 1N NaOH (1×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fddecac2ec004fb285028b74eb0ac7d7
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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