Hydrochloric Acid → 5-Nitro-indan-2-ylamine hydrochloride

HRID 1814773Notes

Reaction equation

HRID 1814773 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13]C(=O)C)[CH2:7]2)([O-:3])=[O:2].[ClH:17]>>[ClH:17].[NH2:13][CH:8]1[CH2:7][C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:9]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 14820512N-(5-nitro-indan-2-yl)-acetamide

Product 1

HCID 223193245-Nitro-indan-2-ylamine hydrochloride

Procedure

To N-(5-nitro-indan-2-yl)-acetamide (23.5 g, 107 mmol) is added 2N hydrochloric acid (500 mL). The mixture is heated to reflux for 24 h and then concentrated in vacuo. Methanol (100 mL) is added to the residue and the mixture is concentrated in vacuo. Toluene (100 mL) is added and the mixture is again concentrated. A solution of the residue in methanol (100 mL) is warmed, diethyl ether (500 mL) is added and the mixture is let stand overnight. The solid is collected by filtration and air dried to yield 2-amino-5-nitroindane hydrochloride as a white solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 h
  3. concentrationconcentrated in vacuo
  4. additionMethanol (100 mL) is added to the residue
  5. concentrationthe mixture is concentrated in vacuo
  6. additionToluene (100 mL) is added
  7. concentrationthe mixture is again concentrated
  8. temperatureA solution of the residue in methanol (100 mL) is warmed
  9. additiondiethyl ether (500 mL) is added
  10. filtrationThe solid is collected by filtration and air
  11. customdried

Sources & evidence

ORD record
ord-5551f9a7e51f4eb58cad8f44d790f270
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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