Ammonium Chloride → HCID 20120397, compound

HRID 555404Notes

Reaction equation

HRID 555404 reaction equation
[N+:1]([C:4]1[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C.[Zn]>[NH2:1][C:4]1[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 18194855HCID 18194855, compound

Product 1

HCID 20120397HCID 20120397, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude reaction mixture from 106a was dissolved in ethanol (4 mL) and ethyl acetate (1 mL). Zinc dust (1.3 g, 20 mmol) was added to the mixture along with ammonium chloride (300 mg, 5.7 mmol). The mixture was shaken at rt for 18 h. The reaction mixture was filtered over Celite®, and concentrated to afford mainly 106b which was used in the next step without further purification. [M+H]+=212.32.

Workup

  1. filtrationThe reaction mixture was filtered over Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d11236c679964d0f988e415c459065c3
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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