Ethanol → 865716-15-0

HRID 1373753Notes

Reaction equation

HRID 1373753 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[N+:12]([O-])=O)[CH:2]=[CH2:3].[NH4+].[Cl-].C(O)C>[Fe].O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[NH2:12])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 21075356HCID 21075356, compound

Product 1

HCID 21075371865716-15-0Yield 100.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of Example 66A (5.06 g, 19.69 mmol), iron powder (11.02 g, 196.9 mmol), NH4Cl (0.53 g, 9.85 mmol), ethanol (160 mL), and water (40 mL) were heated at 80° C. for 6 hours. The solution was filtered, concentrated with silica gel powder (18 g), and purified by flash chromatography eluting with 10% ethyl acetate in hexanes (1 L) to give the title compound (4.53 g, 97%). MS (DCI) m/z 227.91 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 4.54 (d, J=5.43 Hz, 2 H) 5.29 (dd, J=10.51, 1.36 Hz, 1 H) 5.40 (dd, J=17.46, 1.53 Hz, 1 H) 6.09 (m, 1 H) 6.65 (d, J=8.48 Hz, 1 H) 6.84 (m, 1 H) 6.91 (d, J=2.37 Hz, 1 H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated with silica gel powder (18 g)
  3. custompurified by flash chromatography
  4. washeluting with 10% ethyl acetate in hexanes (1 L)

Sources & evidence

ORD record
ord-a37ec4d6ec16443394e6ce551bcfbb40
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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