Hydrazine hydrate (1:1) → HCID 20094653, compound

HRID 1366878Notes

Reaction equation

HRID 1366878 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:18])[C:8](=O)[CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O)[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[C:9]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[NH:3][N:2]=1)=[O:18])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13245015Ethyl oxo(2-oxocycloheptyl)acetate

Product 1

HCID 20094653HCID 20094653, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.142 mL, 2.94 mmol) was added to a stirring room temperature solution of 13 (0.6229 g, 2.94 mmol) in EtOH (2.9 mL, 1 M) under N2. The reaction was then heated to reflux until judged complete by TLC (4.5 h): The reaction was concentrated and purified by silica gel chromatography (Combiflash column, 70:30:2 Hexanes:CH2Cl2:2N NH3 in EtOH): Only pure fractions were combined and concentrated to obtain 0.4428 g (72.3%) of 14. 1H (CDCl3, 400 MHz): δ 8.56 (1H, broad s), 4.30 (2H, q, J=7.1 Hz), 2.92-2.86 (2H, m), 2.73-2.78 (2H, m), 1.84-1.76 (2H, m), 1.65-1.57 (4H, m), 1.30 (3H, t, J=7.1 Hz) ppm. 13C (CDCl3, 100 MHz): δ 162.11, 150.70, 134.97, 124.58, 60.85, 32.33, 28.63, 28.32, 27.39, 24.42, 14.47 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 14.47; CH2 carbons: 60.85, 32.33, 28.63, 28.32, 27.39, 24.42; ppm. HPLC: 9.19 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. customuntil judged complete by TLC (4.5 h)
  4. concentrationThe reaction was concentrated
  5. custompurified by silica gel chromatography (Combiflash column, 70:30:2 Hexanes:CH2Cl2:2N NH3 in EtOH)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cb4902c03aeb4a6e9a3c0f45b1409e08
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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