Hydrochloric Acid → HCID 86698653, compound

HRID 1054650Notes

Reaction equation

HRID 1054650 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:19]#[N:20])=[CH:11][C:12]([N+:16]([O-])=O)=[C:13]([CH3:15])[CH:14]=2)=[CH:5][CH:4]=1.[CH3:21]N(C(N(C)C)N(C)C)C.Cl>C1(C)C=CC=CC=1.O.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]3[C:12](=[CH:11][C:10]=2[C:19]#[N:20])[NH:16][CH:21]=[CH:15]3)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 86698652HCID 86698652, compound

Product 1

HCID 86698653HCID 86698653, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4′-methoxy-5-methyl-4-nitro-biphenyl-2-carbonitrile (118.0 mg, 0.44 mmol) and tris(dimethylamino) methane (128.0 mg, 0.88 mmol) in toluene (15 mL) was heated to reflux for 2 hours. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in EtOH (1 mL) and water (0.10 mL), and treated with iron powder (64.0 mg, 1.15 mmol), followed by concentrated HCl (28.0 mg, 0.29 mmol). The reaction mixture was heated to reflux for an additional 16 hours, and quenched with 1 N aqueous NaOH (0.288 mL). The solution was filtered through celite and rinsed with EtOH (10 mL). The filtrate was concentrated in vacuo to give the title compound (35 mg, 49% yield). MS (ES−) 247.1 (M−1)−. 1H NMR (400 MHz, DMSO-d6) δ 7.95 (s, 1 H), 7.68 (d, J=2.73 Hz, 1 H), 7.66 (s, 1 H), 7.48 (d, J=8.59 Hz, 2 H), 7.05 (d, J=8.59 Hz, 2 H), 6.58 (d, J=2.73 Hz, 1 H), 3.82 (s, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in EtOH (1 mL)
  5. temperatureThe reaction mixture was heated
  6. temperatureto reflux for an additional 16 hours
  7. customquenched with 1 N aqueous NaOH (0.288 mL)
  8. filtrationThe solution was filtered through celite
  9. washrinsed with EtOH (10 mL)
  10. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-60c7bc1122b34b139178384a542bda92
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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