Ammonium Chloride → HCID 45122650, compound

HRID 1770835Notes

Reaction equation

HRID 1770835 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:6]=2[CH:7]=1)#[N:2].[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:12][C:9]1[CH:10]=[CH:11][C:5]2[O:4][C:3]([C:1]#[N:2])=[CH:7][C:6]=2[CH:8]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 13031366HCID 13031366, compound

Product 1

HCID 45122650HCID 45122650, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
65 °C

Procedure

A heterogeneous reaction mixture of 2-cyano-5-nitrobenzofuran (0.150 g, 0.789 mmol), iron powder (0.220 g, 3.9 mmol), NH4Cl (0.221 g, 3.9 mmol) in EtOH/H2O (5 mL each) was vigorously stirred at 60-70° C. for 1 hour. The resulting solution was filtered through a pad of Celite when hot and then washed with methanol. The filtrated was concentrated to dryness under a vacuum and resuspended into H2O (20 mL), saturated and the solid was isolated by filtration to obtain 5-amino-2-cyanobenzofuran. 1H NMR (DMSO-d6): δ 7.80 (s, 1H), 7.36 (d, 1H, J=8.7 Hz), 6.86 (dd, 1H, J=2.7 and 9.0 Hz), 6.76 (d, 1H, J=2.1 Hz), 5.16 (bs, 2H); LCMS: purity: 95%, MS (m/e): 159 (MH+).

Workup

  1. filtrationThe resulting solution was filtered through a pad of Celite when hot
  2. washwashed with methanol
  3. concentrationThe filtrated was concentrated to dryness under a vacuum
  4. customsaturated and the solid was isolated by filtration

Sources & evidence

ORD record
ord-8e0b5f2c97cf4f6b9b6057382cc602b4
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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