Hydrochloric Acid → HCID 86664826, compound

HRID 1628249Notes

Reaction equation

HRID 1628249 reaction equation
[NH2:1]/[C:2](/[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([Cl:12])[CH:7]=1)=[CH:3]\[C:4]#[N:5].[C:13](O)(=O)[C:14](O)=O.C([NH:21]N)C.Cl>CO>[Cl:12][C:8]1[CH:7]=[C:6]([C:2]2[CH:3]=[C:4]([NH2:21])[N:5]([CH2:13][CH3:14])[N:1]=2)[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 86664827HCID 86664827, compound

Product 1

HCID 86664826HCID 86664826, compoundYield 410.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (Z)-3-amino-3-(2-chloropyridin-4-yl)acrylonitrile 20.2.A (2590 mg, 14420 μmol), and ethylhydrazine oxalate (3220 mg, 2144 μmol) in MeOH (70 mL) was added 2N HCl (18 mL). The reaction was stirred at 80° C. for 2 hr, when LC/MS indicated the completion of the reaction (m/e: 223). The reaction was concentrated and worked up between saturated NaHCO3. and iPrOH/CHCl3. Silica gel chromatography afforded the desired product 20.2.B 1.96 g (61%).

Workup

  1. customthe completion of the reaction (m/e: 223)
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-692e330f34ab4f098d11e6f671132539
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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