HCID 59520005, compound → HCID 53402950, compound

HRID 1162081Notes

Reaction equation

HRID 1162081 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]2[O:9][CH:8]=[C:7](C(O)=O)[C:6]=2[CH:13]=1>N1C2C(=CC=CC=2)C=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:13]=1

Participants

4

Reactant 1

HCID 59520005HCID 59520005, compound

Product 1

HCID 53402950HCID 53402950, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7047QuinolineSolvent

Conditions

Temperature
190 °C

Procedure

5-Bromo-7-nitro-1-benzofuran-3-carboxylic acid (4.65 g, 16 mmol; obtained in Step 2) was suspended in quinoline (25 mL), 0.1 g CuO was added and the mixture heated to 190° C. for 30 minutes. The warm reaction mixture was diluted with hot toluene (100 mL), filtered and the filter cake washed with hot toluene (total 400 mL). The combined toluene extracts were washed with 1 M HCl (2×100 mL) and brine, evaporated and the solid product washed with hexane, collected by filtration and dried. Yield: 1.9 g (48%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.13 (d, J=2.3 Hz, 1H) 8.20 (d, J=2.0 Hz, 1H) 8.28 (d, J=2.3 Hz, 1H) 8.32 (d, J=2.0 Hz, 1H).

Workup

  1. customThe warm reaction mixture
  2. filtrationfiltered
  3. washthe filter cake washed with hot toluene (total 400 mL)
  4. washThe combined toluene extracts were washed with 1 M HCl (2×100 mL) and brine
  5. customevaporated
  6. washthe solid product washed with hexane
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-2329a03cd50e498ca1c297c3280369e9
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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