Potassium Bromide → HCID 12070506, compound

HRID 1096165Notes

Reaction equation

HRID 1096165 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:12]=[C:13]([N+:27]([O-:29])=[O:28])[CH:14]=[C:15]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)=[O:18])[CH:16]=2)=[O:10])=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.[K+].[Br-]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:12]=[C:13]([N+:27]([O-:29])=[O:28])[CH:14]=[C:15]([C:17](=[O:18])[C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[CH:16]=2)=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 10176127Pyridinium chlorideHCID 120705053,5-bis(4-methoxyphenylcarbonyl)nitrobenzene

Product 1

HCID 12070506HCID 12070506, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Into a 250 mL three-necked, round-bottomed flask equipped with a magnetic stirrer, a condenser, and nitrogen inlet, 3,5-bis(4-methoxyphenylcarbonyl) nitrobenzene (6.2 g, 15.8 mmol) and freshly prepared pyridine hydrochloride (100 g) were placed. The mixture was heated under reflux until the solution became homogeneous. It took about 4 h. After cooled down 120° C., the mixture was poured into water. The resulting precipitate was collected and dried. The yellow solid was slurred in boiling toluene and collected by suction filtration to give 5.5 g (96% yield), m.p. 230-231.8° C. Anal. Calcd. for C20H13NO6: C, 66.12%; H, 3.61%; N, 3.86%; O, 26.42%. Found: C, 66.07%; H, 3.64%; N, 3.67%; O, 17.01%. FT-IR (KBr, cm−1): 1321, 1538 (A-NO2), 1602, 1648 (carbonyl), 3420 (Ar—OH). Mass spectrum (m/e): 363 (M+, 100% relative abundance). 1H-NMR (DMSO-d6, δ in ppm): 6.93-6.96 (d, 4H, Ar), 7.76-7.79 (d, 4H, Ar), 8.23 (s, 1H, Ar), 8.58 (s, 2H, Ar), 10.66 (s, 2H, OH). 13C-NMR (DMSO-d6, δ in ppm) 115.48, 126.02, 126.65, 132.84, 134.83, 139.44, 147.61, 156.80, 162.70, 191.36.

Workup

  1. customInto a 250 mL three-necked, round-bottomed flask equipped with a magnetic stirrer, a condenser, and nitrogen inlet
  2. temperatureThe mixture was heated
  3. temperatureunder reflux until the solution
  4. customThe resulting precipitate was collected
  5. customdried
  6. filtrationcollected by suction filtration
  7. customto give 5.5 g (96% yield), m.p. 230-231.8° C

Sources & evidence

ORD record
ord-304175e2876f4c58afd9e0e8423c2321
Source dataset
uspto-grants-2012_03
Patent number
US08138257B1

Reaction notes

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