Ammonium Chloride → HCID 66989945, compound

HRID 2407821Notes

Reaction equation

HRID 2407821 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[C:7]([N+:14]([O-])=O)=[CH:6][CH:5]=1)[CH3:2].[Cl-].[NH4+]>O1CCCC1.O.C(OCC)(=O)C.[Zn]>[NH2:14][C:7]1[C:8]([C:10]([O:12][CH3:13])=[O:11])=[N:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 66989093HCID 66989093, compound

Product 1

HCID 66989945HCID 66989945, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a stirred solution of the compound prepared in Example 425 (0.200 g,) in tetrahydrofuran (4.5 mL) was added zinc dust (0.5782 g), followed by saturated aqueous ammonium chloride (4.5 mL). The mixture was stirred at room temperature for 2 hours. The mixture was diluted with water-ethyl acetate and then filtered through paper. The phases were separated, organic layer dried, concentrated in vacuo and the bright yellow oil purified by column chromatography on silica gel (1-2% methanol in dichloromethane) to provide the title compound (0.132 g) as a yellow oil having the following physical data.

Workup

  1. filtrationfiltered through paper
  2. customThe phases were separated
  3. customorganic layer dried
  4. concentrationconcentrated in vacuo
  5. customthe bright yellow oil purified by column chromatography on silica gel (1-2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e843545d26bd4bccb73aa11ca2ab26d6
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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