HCID 89704741, compound → HCID 89704659, compound

HRID 1051944Notes

Reaction equation

HRID 1051944 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 conc. 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 comb. org. 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. dissolutionredissolved in water (pH 4 with 2N HCl solution)
  4. washIt was washed once with EtOAc
  5. extractionextracted 3 times with EtOAc and DCM
  6. dry with materiallayers were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b18706ac337744f293c5128553a5e623
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

Loading…