Nitric Acid → n-(6-Nitro-2,3-dihydrobenzofuran-5-yl)acetamide

HRID 629679Notes

Reaction equation

HRID 629679 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][CH2:11][CH2:10][C:9]=2[CH:13]=1)(=[O:3])[CH3:2].[N+:14]([O-])([OH:16])=[O:15]>CC(O)=O>[C:1]([NH:4][C:5]1[C:6]([N+:14]([O-:16])=[O:15])=[CH:7][C:8]2[O:12][CH2:11][CH2:10][C:9]=2[CH:13]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 129085765-Acetylamino-2,3-dihydrobenzofuran

Product 1

HCID 13069186n-(6-Nitro-2,3-dihydrobenzofuran-5-yl)acetamideYield 93.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product obtained in Step 3 (6.0 g, 33.9 mmol) was dissolved in AcOH (100 mL), then HNO3 (1.9 mL, 47.5 mmol) was added. The reaction mixture was stirred at room temperature for 1 h, then poured into ice-water. The water layer was extracted with ethyl acetate. The organic layer was dried, concentrated, purified by column chromatography to obtain a product (7.0 g, 93.3%).

Workup

  1. extractionThe water layer was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-edf3e6b8314e4c38a56362f75b2c8904
Source dataset
uspto-grants-2016_04
Patent number
US09315513B2

Reaction notes

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