Hydrochloric Acid → HCID 18670055, compound

HRID 641109Notes

Reaction equation

HRID 641109 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-2a63aa9421a74de19897746d5ac5535c
Source dataset
uspto-grants-2010_04
Patent number
US07695912B1

Reaction notes

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