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

HRID 1531304Notes

Reaction equation

HRID 1531304 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-nitro-indane 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-c3760d2e17784bd7bf76d4a442173bbc
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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