Methyl 7-nitrobenzofuran-4-carboxylate → Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate

HRID 2364661Notes

Reaction equation

HRID 2364661 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:13]([O:15][CH3:16])=[O:14])=[C:8]2[C:12]=1[O:11][CH:10]=[CH:9]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:13]([O:15][CH3:16])=[O:14])=[C:8]2[C:12]=1[O:11][CH2:10][CH2:9]2

Participants

4

Reactant 1

HCID 20738655Methyl 7-nitrobenzofuran-4-carboxylate

Product 1

HCID 68107686Methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylateYield 62.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Methyl 7-nitrobenzofuran-4-carboxylate 1f (820 mg, 3.70 mmol) was dissolved in 150 mL of methanol in an ice-water bath, added with (164 mg, 10%) palladium/carbon, methanol (0.3 mL). The resulting solution was subjected to hydrogenation for 16 hours at 3 atmosphere at room temperature. The resulting mixture was filtered and washed with 50 mL of methanol, concentrated under reduced pressure. The crude residue was recrystallised by the mixture solvent of 25 mL ethyl acetate and n-hexane (V/V=1:4) to obtain the title compound methyl 7-amino-2,3-dihydrobenzofuran-4-carboxylate 1g (446 mg, yield: 62.0%) as a gray solid.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashed with 50 mL of methanol
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was recrystallised by the mixture solvent of 25 mL ethyl acetate and n-hexane (V/V=1:4)

Sources & evidence

ORD record
ord-2d982ef75d1a4446a41cb0a5153faed8
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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