Semicarbazide hydrochloride → 4-(4-Chloro-2-pyridinoxy)benzaldehyde semicarbazone

HRID 1166302Notes

Reaction equation

HRID 1166302 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)[CH:3]=1.Cl.[NH2:18][NH:19][C:20]([NH2:22])=[O:21].O.O.O.C([O-])(=O)C.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[N:18][NH:19][C:20]([NH2:22])=[O:21])=[CH:11][CH:10]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 234332144-[(4-Chloro-2-pyridinyl)oxy]benzaldehydeHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 544491214-(4-Chloro-2-pyridinoxy)benzaldehyde semicarbazoneYield 96.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(4-chloro-2-pyridinoxy)benzaldehyde (330 mg, 1.41 mmol) in ethanol (10 mL) was added a solution of semicarbazide hydrochloride (213 mg, 1.84 mmol) and sodium acetate trihydrate (224 mg, 1.65 mmol) in water (5 mL). The mixture was stirred at room temperature for 30 min., and the resulting solid was collected by filtration, washed with water and dried in vacuo to yield the title compound as a white solid (400 mg, 1.36 mmol, 96%), mp: 231-233° C. 1H NMR (DMSO-d6): δ 10.22 (s, 1H), 8.22 (d, J=2.5, 1H), 7.97 (dd, J=2.5, 8.7, 1H), 7.85 (s, 1H), 7.77 (d, J=8.7, 2H), 7.15 (d, J=8.7, 2H) 7.12 (d, J=8.7, 1H), 6.47 (s, 2H).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-015bc2343cfb4fa392050479539ab217
Source dataset
uspto-grants-2003_09
Patent number
US06613803B1

Reaction notes

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