Water → HCID 21696862, compound

HRID 378854Notes

Reaction equation

HRID 378854 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:5]=2[C:6]=1[N+:7]([O-:9])=[O:8].O.[OH-].[Na+]>C(OCC)(=O)C>[CH3:1][C:2]1[O:3][C:4]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:5]=2[C:6]=1[N+:7]([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 2798472-methyl-3,5-dinitro-1-benzofuran

Product 1

HCID 21696862HCID 21696862, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-3,5-dinitrobenzofuran (4.4 g, 19.8 mmol) in ethyl acetate (250 mL) was added stannous chloride (dihydrate, 8.99 g, 39.8 mmol). The mixture was stirred at room temperature for 70 hours. Water (100 mL) and 1N NaOH (100 mL) were added. The mixture was extracted with ethyl acetate (4×150 mL). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed (silica, 20-30% ethyl acetate in hexanes) to give 2-methyl-3-nitro-5-benzofuranamine as a yellow solid (1.71 g, 45%): 1H-NMR (270 MHz, CDCl3) δ 7.38 (d, 1H, J=2.8 Hz), 7.25 (d, 1H, J=8.8 Hz), 6.72 (dd, 1H, J=8.8, 2.8 Hz), 2.87 (s, 3H); HPLC (Method A) tR=1.36 min.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (4×150 mL)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was chromatographed (silica, 20-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-46fa2750f0dc4f3783f0d7e2c6ae51f3
Source dataset
uspto-grants-2001_10
Patent number
US06297233B1

Reaction notes

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