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HCID 58504230, compound → HCID 58504273, compound

HRID 2407688
Notes
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Reaction equation

HRID 2407688 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][O:10][C:6]=2[C:5](NN)=[N:4][N:3]=1>C1C=CC=CC=1.C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][O:10][C:6]=2[CH:5]=[N:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 58504230HCID 58504230, compound

Product 1

HCID 58504273HCID 58504273, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

The compound prepared in Example 81 (4.40 g) was dissolved in benzene (500 mL)-ethanol (50 mL) and 1 mol/L aqueous sodium hydroxide (67.0 mL) was added. This mixture was cooled to 0° C. Oxygen was bubbled through the vigorously stirred mixture for 30 minutes. The mixture was separated and the aqueous portion was extracted with dichloromethane. The combined organics were washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to obtain the title compound (2.53 g) having the following physical data.

Workup

  1. additionwas added
  2. customOxygen was bubbled through the vigorously stirred mixture for 30 minutes
  3. customThe mixture was separated
  4. extractionthe aqueous portion was extracted with dichloromethane
  5. washThe combined organics were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-a72affea3a0b4381a2b307ce574c0bc4
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809538B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes