Ethyl Acetate → HCID 89922410, compound

HRID 921868Notes

Reaction equation

HRID 921868 reaction equation
[Cl:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:14]1=[O:20].[Cl-].[NH4+].C(=O)(O)[O-].[Na+].CCOC(C)=O>CO.[Zn]>[NH2:10][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:14]2=[O:20])[C:2]=1[Cl:1])[C:6]#[N:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 899234104-Chloro-3-(4-methyl-2-oxo-1-piperazinyl)-5-nitrobenzonitrile

Product 1

HCID 89922410HCID 89922410, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-3-(4-methyl-2-oxopiperazin-1-yl)-5-nitrobenzonitrile (40 mg, 0.136 mmol) in MeOH (4 mL) was added ammonium chloride (218 mg, 4.07 mmol) and zinc (133 mg, 2.036 mmol) (in two portions, after the first portion, reaction was not complete). After stirring at room temperature for 12 h. LC-MS indicated completion. Then 5 mL of saturated aqueous sodium bicarbonate solution was added followed by 10 mL of EtOAc. The mixture was filtered through a pad of Celite and the filter cake was washed EtOAc. The solvent from the filtrate was evaporated. Purification via flash chromatography (0-10% MeOH in DCM, 24 g) gave 3-amino-4-chloro-5-(4-methyl-2-oxopiperazin-1-yl)benzonitrile (28 mg) as an off-white solid.

Workup

  1. customafter the first portion, reaction
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washthe filter cake was washed EtOAc
  4. customThe solvent from the filtrate was evaporated
  5. customPurification via flash chromatography (0-10% MeOH in DCM, 24 g)

Sources & evidence

ORD record
ord-fc85f0be09a744b1904f4b882e4cf220
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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