Hydrochloric Acid → HCID 69287051, compound

HRID 2220585Notes

Reaction equation

HRID 2220585 reaction equation
Br[C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][C:12]3[O:13][C:14]4[CH:20]=[CH:19][CH:18]=[C:17](Br)[C:15]=4[CH:16]=3)[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:22]([Cu])#[N:23].Cl.[N:26]1C2C(=CC=CC=2)C=C[CH:27]=1>>[C:27]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([C:22]#[N:23])=[CH:17][C:15]=4[CH:16]=3)=[CH:8][C:7]=2[CH:2]=1)#[N:26]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 23657703HCID 23657703, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69287051HCID 69287051, compoundYield 63%

Conditions

Temperature
60 °C

Procedure

A mixture of bis(6-bromobenzofuran-2-yl)methanone (84) (3.50 g, 8.62 mmol) and CuCN (6.12 g, 69.0 mmol) was heated under reflux in dry quinoline (10 mL) for 2 hours. The hot reaction mixture was poured into 2 M HCl solution and resulting mixture was stirred at 50-70° C. for 1 hour. Olive precipitate was filtered off, dried under high vacuum and suspended into 300 mL chlorobenzene. The mixture was stirred for 1 hour at room temperature, insoluble material was separated, and filtrate was concentrated. A dark solid residue (2 g, 78%) was purified by column chromatography (SiO2, CHCl3) to afford desired product as light yellow crystals (1.62 g, 63%): mp 173-174° C. (CHCl3). 1H NMR (DMSO-d6) δ7.96 (d, J=8.2 Hz, 2H), 7.77 (d, J=7.7 Hz, 2H), 7.46 (tt, J=8.2, 7.7 Hz, 2H), 7.09 (s, 2H), 4.64 (s, 2H). HPLC (method B) tR 7.92 min (100.00 area %). Anal. (C19H10N2O2) C, H, N.

Workup

  1. temperaturewas heated
  2. customresulting mixture
  3. filtrationOlive precipitate was filtered off
  4. customdried under high vacuum
  5. stirringThe mixture was stirred for 1 hour at room temperature
  6. custominsoluble material was separated
  7. concentrationfiltrate was concentrated
  8. customA dark solid residue (2 g, 78%) was purified by column chromatography (SiO2, CHCl3)

Sources & evidence

ORD record
ord-61a8f35a63f1490986144f75aceb8096
Source dataset
uspto-grants-2008_08
Patent number
US07417158B2

Reaction notes

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