Ammonium Chloride → 4-(Prop-2-yn-1-yloxy)aniline

HRID 1947588Notes

Reaction equation

HRID 1947588 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)[C:2]#[CH:3].[NH4+].[Cl-]>CCO.O.[Fe]>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[C:2]#[CH:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 31171181-Nitro-4-(prop-2-ynyloxy)benzene

Product 1

HCID 126688624-(Prop-2-yn-1-yloxy)aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

4-(Prop-2-ynyloxy)nitrobenzene (0.910 g, 5.13 mmol), iron (1.42 g, 25.3 mmol), and NH4Cl (0.719 g, 12.8 mmol) were vigorously stirred in EtOH/water (1:1, 55 mL) at 70° C. for 15 minutes. The reaction mixture was filtered hot through Celite and concentrated in vacuo. The residue was suspended in 10% 2N ammoniacal methanol in dichloromethane, sonicated, and filtered through Celite. Concentration gave 4-(prop-2-ynyloxy)aniline as a brown oil which was used without further purification. In general, isolated prop-2-ynyloxyanilines were unstable and were therefore used immediately after the second filtration. 1H NMR (CDCl3): δ 6.82 (d, J=8.7 Hz, 2H), 6.64 (d, J=8.7 Hz, 2H), 4.61 (d, J=2.4 Hz, 2H), 2.50 (t, J=2.4 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered hot through Celite
  2. concentrationconcentrated in vacuo
  3. customsonicated
  4. filtrationfiltered through Celite
  5. concentrationConcentration

Sources & evidence

ORD record
ord-55e4177a970340c7aa9e844dc1a69f0d
Source dataset
uspto-grants-2013_03
Patent number
US08399472B2

Reaction notes

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