Hydrazinium chloride → HCID 178470498, compound

HRID 1520774Notes

Reaction equation

HRID 1520774 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9](=O)/[C:10](/[CH3:18])=[C:11](\[O-])/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2].[Li+].Cl.[NH2:22][NH2:23]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[NH:23][N:22]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]=2[CH3:18])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 86674807HCID 86674807, compound

Product 1

HCID 178470498HCID 178470498, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of lithium (Z)-4-(3-cyanophenyl)-1-ethoxy-3-methyl-1,4-dioxobut-2-en-2-olate (400 mg, 1.51 mmol, Eq: 1.00) in Ethanol (10 ml) was added Hydrazine hydrochloride (113 mg, 1.65 mmol, Eq: 1.093) at rt to give an orange solution. The resulting mixture was stirred overnight at the same temperature. After 1 day the solvent was removed under reduce pressure and to the mixture was added brine. The solution was extracted two times with AcOEt, and the combined organic layers were dried over MgSO4, filtered and concentrated to give the desired compound as a yellow gum (114 mg, 26.6%). MS (ISP): 256.0 ([M+H]+).

Workup

  1. customto give an orange solution
  2. customAfter 1 day the solvent was removed
  3. additionto the mixture was added brine
  4. extractionThe solution was extracted two times with AcOEt
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3c94a0681dd942ed8b6e075aa974b358
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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