Acetic Acid → HCID 77231503, compound

HRID 2362154Notes

Reaction equation

HRID 2362154 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](Cl)[N:5]2[N:15]=[CH:16][N:17]=[C:4]2[N:3]=1.CC(O)=O.CO>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:15]=[CH:16][N:17]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 11149750HCID 11149750, compound

Product 1

HCID 77231503HCID 77231503, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-3 (100 mg, 0.37 mmol) in a co-solvent of AcOH (0.2 mL), MeOH (0.2 mL) and THF (1.2 mL) was added Zn/Cu pair (73 mg, 0.6 mmol) and the mixture was stirred at r.t. for 3 h. The mixture was filtered to remove the insoluble solid and the filtrate was diluted with 15 mL of DCM, the combined organic phase was washed with 0.1N HCl aq. and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 43 mg of 3-4.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the insoluble solid
  3. additionthe filtrate was diluted with 15 mL of DCM
  4. washthe combined organic phase was washed with 0.1N HCl aq. and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by prep.TLC

Sources & evidence

ORD record
ord-283f6b0d81e241648e6b946358c63479
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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