Acetic Acid → HCID 67228647, compound

HRID 2275312Notes

Reaction equation

HRID 2275312 reaction equation
[C:1]([CH:3]1[CH2:9][CH2:8][CH2:7][N:6]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[C:5]2[C:4]1=O)#[N:2].O.[NH2:20][NH2:21].C(O)(=O)C>C(O)C>[NH2:2][C:1]1[C:3]2[CH2:9][CH2:8][CH2:7][N:6]3[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[C:5]3[C:4]=2[NH:21][N:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 67228645HCID 67228645, compound

Product 1

HCID 67228647HCID 67228647, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethyl 8-cyano-9-oxo-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine-2-carboxylate (12 g, 49 mmol) in ethanol a solution of hydrazine monohydrate (6.5 g, 130 mmol) and acetic acid (9 g, 150 mmol) was added. The reaction was refluxed for 62 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and NH3. The organic phase was dried on Na2SO4. 10 g of a pale yellow solid were obtained (yield 78%).

Workup

  1. temperatureThe reaction was refluxed for 62 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and NH3
  5. customThe organic phase was dried on Na2SO4

Sources & evidence

ORD record
ord-4414727c5a7d41e1bda0d1bc4a59a97e
Source dataset
uspto-grants-2015_09
Patent number
US09127015B2

Reaction notes

Loading…