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

HRID 648223Notes

Reaction equation

HRID 648223 reaction equation
[N+:1]([C:4]1[C:5]([NH:13]C(=O)C)=[CH:6][C:7]2[CH2:11][CH2:10][O:9][C:8]=2[CH:12]=1)([O-:3])=[O:2]>C(O)C.Cl>[N+:1]([C:4]1[C:5]([NH2:13])=[CH:6][C:7]2[CH2:11][CH2:10][O:9][C:8]=2[CH:12]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 13069186n-(6-Nitro-2,3-dihydrobenzofuran-5-yl)acetamide

Product 1

HCID 130691876-Nitro-2,3-dihydrobenzofuran-5-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

89 g of N-(6-nitro-2,3-dihydrobenzo[b]furan-5-yl)acetamide in 1 l of ethanol and 400 ml of hydrochloric acid is refluxed for 2 hours and concentrated. The residue is combined with 2 N sodium hydroxide solution/ethyl acetate, the aqueous phase is again extracted once with ethyl acetate, and the combined organic phases are concentrated, thus obtaining from ethyl acetate 66 g of 6-nitro-2,3-dihydrobenzo[b]furan-5-amine, mp 152° C.

Workup

  1. concentrationconcentrated
  2. extractionthe aqueous phase is again extracted once with ethyl acetate
  3. concentrationthe combined organic phases are concentrated

Sources & evidence

ORD record
ord-d077766a5f5d418db239430ef823eae8
Source dataset
uspto-grants-1983_10
Patent number
US04411910

Reaction notes

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