HCID 89704741, compound → HCID 89704659, compound

HRID 1481339Notes

Reaction equation

HRID 1481339 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:9]=1[CH:16]=[N:17]O)(=O)C>CC(O)=O.[Zn]>[NH2:17][CH2:16][C:9]1[C:10]([Cl:15])=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=1[O:7][CH2:6][CH2:5][OH:4]

Participants

4

Reactant 1

HCID 89704741HCID 89704741, compound

Product 1

HCID 89704659HCID 89704659, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2-(3,5-dichloro-2-((hydroxyimino)methyl)phenoxy)ethyl acetate (1.15 mmol) in 2 mL AcOH was cooled to 0° C. and zinc dust (4.36 mmol) was added. The reaction mixture was stirred at RT for 1 h. It was filtered over a pad of celite and washed with EtOAc and MeOH. The filtrate was concentrated and redissolved in water (pH 4 with 2N HCl solution). It was washed once with EtOAc, the ageous phase was basified with 1M NaOH solution, extracted 3 times with EtOAc and DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as white solid.

Workup

  1. filtrationIt was filtered over a pad of celite
  2. washwashed with EtOAc and MeOH
  3. concentrationThe filtrate was concentrated
  4. dissolutionredissolved in water (pH 4 with 2N HCl solution)
  5. washIt was washed once with EtOAc
  6. extractionextracted 3 times with EtOAc and DCM
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db91ff03e22a4617a1d7219e4c51fb0e
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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