Ammonium Chloride → HCID 69507735, compound

HRID 1375676Notes

Reaction equation

HRID 1375676 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:9]=2[N+:18]([O-])=O)[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:18][C:9]1[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][O:12][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 69507602HCID 69507602, compound

Product 1

HCID 69507735HCID 69507735, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

This material from Example 21B was dissolved in a mixture of EtOH (6 mL) and water (2 mL). Ammonium chloride (160 mg, 3 mmol) and iron powder (1.6 g, 28 mmol) were added at r.t. The reaction mixture was filtered after 1 h. The filtrate was extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried over MgSO4, concentrated, and purified by flash column chromatography (20% ethyl acetate in hexanes) to provide the titled compound (390 mg, 17% for two steps).

Workup

  1. filtrationThe reaction mixture was filtered after 1 h
  2. extractionThe filtrate was extracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-200e7ea87b164e81a4c258171d47ecca
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

Loading…