Hydrochloric Acid → HCID 86673525, compound

HRID 1424555Notes

Reaction equation

HRID 1424555 reaction equation
Cl[Sn]Cl.Cl.[N+:5]([C:8]1[C:9]([C:26]#[C:27][C:28]2[C:33]([F:34])=[C:32]([F:35])[N:31]=[C:30]([F:36])[C:29]=2[F:37])=[C:10]([C:14]#[C:15][C:16]2[C:21]([F:22])=[C:20]([F:23])[N:19]=[C:18]([F:24])[C:17]=2[F:25])[CH:11]=[CH:12][CH:13]=1)([O-])=O>C1COCC1>[F:36][C:30]1[C:29]([F:37])=[C:28]([C:27]#[C:26][C:9]2[C:10]([C:14]#[C:15][C:16]3[C:21]([F:22])=[C:20]([F:23])[N:19]=[C:18]([F:24])[C:17]=3[F:25])=[CH:11][CH:12]=[CH:13][C:8]=2[NH2:5])[C:33]([F:34])=[C:32]([F:35])[N:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 86673524HCID 86673524, compound2×

Product 1

HCID 86673525HCID 86673525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

SnCl2 (5.8 g, 31 mmol) and 1.5 mL of conc. HCl (aq) were added to the solution of 4,4′-((3-Nitro-1,2-phenylene)bis (ethyne-2, 1-diyl))bis (2,3,5,6-tetrafluoropyridine), (18) (1.45 g, 3.1 mmol) in 30 mL of THF. The reaction mixture was stired for 1 day. After basification till pH>9 with NaOH (1.0 N solution), the product was extracted with dichloromethane. Solvent was evaporated and 0.4 g (31%) of the product aniline was purified by recrystallization: 1H-NMR (300 MHz, CDCl3) δ 7.29 (m, 1H), 7.09 (d, J=7.8 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 4.58 (s, 2H)

Workup

  1. extractionAfter basification till pH>9 with NaOH (1.0 N solution), the product was extracted with dichloromethane
  2. customSolvent was evaporated
  3. custom0.4 g (31%) of the product aniline was purified by recrystallization

Sources & evidence

ORD record
ord-572f0de9d78f44a08bf167445d914174
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

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