Methyl 2-methyl-7-nitro-2,3-dihydrobenzofuran-4-carboxylate → Methyl 7-amino-2-methyl-2,3-dihydrobenzofuran-4-carboxylate

HRID 2364732Notes

Reaction equation

HRID 2364732 reaction equation
[CH3:1][CH:2]1[CH2:6][C:5]2=[C:7]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:9][C:10]([N+:11]([O-])=O)=[C:4]2[O:3]1.[H][H]>CO.[Pd]>[NH2:11][C:10]1[CH:9]=[CH:8][C:7]([C:14]([O:16][CH3:17])=[O:15])=[C:5]2[C:4]=1[O:3][CH:2]([CH3:1])[CH2:6]2

Participants

5

Reactant 2

HCID 68107419Methyl 2-methyl-7-nitro-2,3-dihydrobenzofuran-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68107846Methyl 7-amino-2-methyl-2,3-dihydrobenzofuran-4-carboxylateYield 91.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-methyl-7-nitro-2,3-dihydrobenzofuran-4-carboxylate 30a (100 mg, 0.42 mmol) was dissolved in 20 mL of methanol followed by the addition of palladium/carbon (10 mg, 10%), filled with hydrogen for three times. The reaction solution was stirred for 12 hours and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound methyl 7-amino-2-methyl-2,3-dihydrobenzofuran-4-carboxylate 30b (80 mg, yield: 91.0%) as a colorless oil liquid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-650d439649754ea690b74b723fcf9474
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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