Sodium Carbonate → Methyl 7-amino-2,2-dimethyl-2,3-dihydrobenzofuran-4-carboxylate

HRID 2364681Notes

Reaction equation

HRID 2364681 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:6][C:5]2=[C:7]([C:14]([O-:16])=[O:15])[CH:8]=[CH:9][C:10]([N+:11]([O-])=O)=[C:4]2[O:3]1.[C:18](=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.[Fe]>[NH2:11][C:10]1[CH:9]=[CH:8][C:7]([C:14]([O:16][CH3:18])=[O:15])=[C:5]2[C:4]=1[O:3][C:2]([CH3:17])([CH3:1])[CH2:6]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 866682462,2-Dimethyl-7-nitro-3H-benzofuran-4-carboxylate

Product 1

HCID 68107595Methyl 7-amino-2,2-dimethyl-2,3-dihydrobenzofuran-4-carboxylateYield 74.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

2,2-Dimethyl-7-nitro-3H-benzofuran-4-carboxylate 4c (1.20 g, 4.77 mmol) and iron powder (0.80 g, 14.32 mmol) were dissolved in 25 mL of acetic acid. The reaction mixture was stirred for 12 hours. The resulting mixture was added with sodium carbonate and solid sodium bicarbonate to adjust pH to 7 to 8, extracted with ethyl acetate (50 mL×3). The combined organic phase was washed with water (30 mL) and saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 7-amino-2,2-dimethyl-3H-benzofuran-4-carboxylate 4d (789 mg, yield: 74.6%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. washThe combined organic phase was washed with water (30 mL) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7667827a15f84c7ab3f2a1a2e5605c00
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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