HCID 131736104, compound → HCID 82627609, compound

HRID 1481336Notes

Reaction equation

HRID 1481336 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][CH3:13])[C:3]=1[CH:4]=[N:5]O>CC(O)=O.[Zn]>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][CH3:13])[C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 1

HCID 131736104HCID 131736104, compound

Product 1

HCID 82627609HCID 82627609, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2,4-dichloro-6-methoxybenzaldehyde oxime (2.24 mmol) in 3 mL AcOH was cooled to 0° C. and zinc dust (8.53 mmol) was added. The reaction mixture was stirred at RT for 2 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 yellow 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-ea5831008852418abe961c856d9d4d63
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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