Water → HCID 140606546, compound

HRID 920947Notes

Reaction equation

HRID 920947 reaction equation
[Cl:1][C:2]1[CH:12]=[N:11][CH:10]=[C:9]([CH:13]=O)[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:15]([NH:18][NH2:19])(=[O:17])[CH3:16].C(Cl)Cl.O>C(O)C>[C:15]([NH:18]/[N:19]=[CH:13]/[C:9]1[CH:10]=[N:11][CH:12]=[C:2]([Cl:1])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14039AcetohydrazideHCID 86683163HCID 86683163, compound

Product 1

HCID 140606546HCID 140606546, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 3-chloro-5-formylisonicotinate (2 g, 9.36 mmol) in 60 mL of ethanol was added acetohydrazide (0.832 g, 11.24 mmol) at room temperature. The reaction mixture was stirred for 2 h. Then, the reaction mixture was mixed with DCM and water. The organic phase was washed with brine, dried and concentrated. The crude title compound was purified by chromatography (eluent: DCM/methanol) to give 220 mg (8.7%) of the title compound as orange oil.

Workup

  1. washThe organic phase was washed with brine
  2. customdried
  3. concentrationconcentrated
  4. customThe crude title compound was purified by chromatography (eluent: DCM/methanol)

Sources & evidence

ORD record
ord-86379242d9634b108bdb63c8688bfc12
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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