Hydrazine hydrate (1:1) → HCID 14953504, compound

HRID 470903Notes

Reaction equation

HRID 470903 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][C:9]2[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.O.[NH2:23][NH2:24]>C(O)C>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([NH:23][NH2:24])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12398532HCID 12398532, compound

Product 1

HCID 14953504HCID 14953504, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 250 mL round bottomed flask was charged with ethyl 4-(4-methoxybenzyloxy)benzoate (11.45 g, 60.18 mmol) and ethanol (110 mL). Hydrazine monohydrate was then added and the mixture was placed under reflux for 48 h. The reaction mixture was concentrated to dryness and chloroform (150 mL) was added. The mixture was decanted and the insoluble white residue was washed once more with chloroform to remove traces of starting material. The white solid (5.3 g, 32%) was dried in vacuo and 1H NMR analysis was consistent with the title compound. 1H NMR (DMSO d6, 400 MHz) δ 9.6 (br s, 1 H), 7.77 (d, J=9 Hz, 2 H), 7.36 (d, J=9 Hz, 2 H), 7.03 (d, J=9 Hz, 1 H), 6.94 (d, J=9 Hz, 1 H), 5.05 (s, 2 H), 3.74.

Workup

  1. temperatureunder reflux for 48 h
  2. concentrationThe reaction mixture was concentrated to dryness and chloroform (150 mL)
  3. additionwas added
  4. customThe mixture was decanted
  5. washthe insoluble white residue was washed once more with chloroform
  6. customto remove traces of starting material
  7. dry with materialThe white solid (5.3 g, 32%) was dried in vacuo and 1H NMR analysis

Sources & evidence

ORD record
ord-f3b776c3dc2e419e8d11b9316fa21b1e
Source dataset
uspto-grants-2014_01
Patent number
US08629167B2

Reaction notes

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