Hydrochloric Acid → HCID 18670055, compound

HRID 885777Notes

Reaction equation

HRID 885777 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([N+:23]([O-])=O)[CH:12]=[CH:13][C:14]=2[C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[Sn]Cl.Cl>C1COCC1>[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([NH2:23])[CH:12]=[CH:13][C:14]=2[C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 12149206HCID 12149206, compound

Product 1

HCID 18670055HCID 18670055, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,4-bis(phenylethynyl)nitrobenzene (2.5 g, 7.7 mmol), SnCl2 (7.3 g, 39 mmol, 5 eq.), and HCl (5 mL, 10 eq.) in THF (20 mL) was stirred at room temperature for 5 h. After neutralization with NaOH (1.0N solution), product was extracted with dichloromethane. Solvent was evaporated and the residue was purified by column chromatography on silica gel using chloroform as the eluent to yield 1.7 g (75%) of 3,4-bis(phenylethynyl)phenylamine as a brown oil. 1H NMR (300 MHz, CDCl3) δ 7.67-7.61 (m, 4H), 7.42-7.35 (m, 7H), 6.85 (d, J=2.4 Hz, 1H), 6.62-6.58 (dd, J=2.4 Hz, J=8.4 Hz, 1H), 3.85 (broad, 1H). 13C NMR (68 MHz, CDCl3) δ 146.3, 132.9, 131.5, 131.2, 131.8, 128.3, 128.2, 127.7, 126.5, 123.7, 123.1, 117.3, 117.2, 115.1, 114.9, 92.8, 91.2, 88.9, 88.5. m/z (high res. ESI) 294.1283 (Calc. C22H16N 294.1283).

Workup

  1. extractionAfter neutralization with NaOH (1.0N solution), product was extracted with dichloromethane
  2. customSolvent was evaporated
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e0ba554c8f4c49c7bed6d1c3645029db
Source dataset
uspto-grants-2012_08
Patent number
US08242307B1

Reaction notes

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