Hydrochloric Acid → HCID 178431722, compound

HRID 2396471Notes

Reaction equation

HRID 2396471 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10](I)=[C:9]([O:14]C)[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1.[CH3:18][Sn](C)(C)C.[F-].[K+].Cl>C1(C)C=CC=CC=1.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([CH3:18])=[C:9]([OH:14])[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11661TetramethyltinHCID 522689Potassium FluorideHCID 18980002HCID 18980002, compound

Product 1

HCID 178431722HCID 178431722, compound

Reagents, catalysts & solvents 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)CatalystHCID 1140TolueneSolvent

Procedure

8-Chloro-4-iodo-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (0.50 g) was suspended in toluene (12 mL) and trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) (50 mg) and tetramethyltin (0.30 mL) were added. The mixture was allowed to reflux for 17 hours, was cooled to room temperature, and 10% (w/w) aqueous potassium fluoride (3 mL) was added, followed by 3N hydrochloric acid (10 mL). The resulting mixture was warmed to 50 ° C. for 6 hours. The reaction mixture was filtered, and the crude product was washed (water, hexane). Crystallization, twice, from dimethylformamide and water gave the title compound as an off-white solid (110 mg); mp 277°-279 ° C.; NMR: 11.72 (s,1), 10.28 (s,1), 7.95 (d,1, J=8.7), 7.48 (t,1, J=2.0), 7.31 (dd,1, J=8.7, 2.0), 2.07 (s,1). Analysis for C11H8ClNO3 ·0.10 H2 0: Calculated: C, 55.18; H, 3.45; N, 5.85; Found: C, 55.23; H, 3.47; N, 5.83.

Workup

  1. temperatureto reflux for 17 hours
  2. temperatureThe resulting mixture was warmed to 50 ° C. for 6 hours
  3. filtrationThe reaction mixture was filtered
  4. washthe crude product was washed (water, hexane)
  5. customCrystallization

Sources & evidence

ORD record
ord-4fe5350af2c6480a92fbbdf8f804009e
Source dataset
uspto-grants-1996_02
Patent number
US05492905

Reaction notes

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