2-AMINOCARBONYL-5-NITROBENZOFURAN → HCID 13031366, compound

HRID 1770834Notes

Reaction equation

HRID 1770834 reaction equation
[NH2:1][C:2]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:7]=2[CH:8]=1)=O>O=P(Cl)(Cl)Cl>[C:2]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:7]=2[CH:8]=1)#[N:1]

Participants

3

Reactant 1

HCID 13829552-AMINOCARBONYL-5-NITROBENZOFURAN

Product 1

HCID 13031366HCID 13031366, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A heterogeneous solution of 2-aminocarbonyl-5-nitrobenzofuran (0.206 g, 1 mmol) in POCl3 (5 mL) was heated at 100° C. for 24 to give a clear solution. The resulting clear solution was carefully poured over ice-water to give a solid mass which was isolated by filtration followed by washing with water to give 2-cyano-5-nitrobenzofuran. 1H NMR (DMSO-d6): δ 8.80 (d, 1H, J=2.4 Hz), 8.42 (dd, 1H, J=2.7 and 9.0 Hz), 8.27 (s, 1H), 7.99 (d, 1H, J=8.7 Hz); LCMS: purity: 98%, MS (m/e): 189 (MH+).

Workup

  1. customto give a clear solution
  2. customto give a solid mass which
  3. customwas isolated by filtration
  4. washby washing with water

Sources & evidence

ORD record
ord-9edba8b77e06481fa5913f5c0b7c9542
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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