Ethanol → HCID 135819170, compound

HRID 1011423Notes

Reaction equation

HRID 1011423 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.O=S(Cl)Cl.O.C([O-])([O-])=O.[Na+].[Na+].[CH3:26][CH2:27]O>>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([O:14][CH2:26][CH3:27])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 1361076117-Hydroxyquinoline-3-carboxylic acid

Product 1

HCID 135819170HCID 135819170, compoundYield 64%

Procedure

To a solution of the compound obtained in stage A (15 g, 79 mmol) in EtOH (500 ml) was added dropwise SOCl2 (40 mL). The resulting mixture was stirred under reflux during 12 hours. After adding water (200 mL), the pH was adjusted to 7.0 with 20% aqueous Na2CO3. The aqueous solution was extracted with CH2Cl2 (3×200 mL). The combined organic layers were dried over MgSO4, filtered and evaporated to afford 11 g (yield: 64%) of the product of molecular formula C12H11NO3. Aspect: pale brown powder.

Workup

  1. temperatureunder reflux during 12 hours
  2. extractionThe aqueous solution was extracted with CH2Cl2 (3×200 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-906707339050480d8e32e713657091ad
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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