1,2,3,4-Tetrahydroisoquinoline-5-carbonitrile → HCID 89499971, compound

HRID 1525366Notes

Reaction equation

HRID 1525366 reaction equation
[CH2:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH2:4][CH2:3][NH:2]1>C(Cl)Cl.O=[Mn]=O>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH2:4][CH2:3][N:2]=1

Participants

4

Reactant 1

HCID 162443971,2,3,4-Tetrahydroisoquinoline-5-carbonitrile

Product 1

HCID 89499971HCID 89499971, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

1,2,3,4-tetrahydroisoquinoline-5-carbonitrile (0.338 g, 2.137 mmol) was oxidized with MnO2 (2.79 g, 32.0 mmol) in DCM (30 mL) over night. Filtered through Celite® and concentrated to yield 0.313 g (94%) of desired product as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.36 (1H, t, J=2.3 Hz), 7.67 (1H, dd, J=7.7, 1.4 Hz), 7.47-7.54 (1H, m), 7.43 (1H, d, J=7.8 Hz), 3.88 (2H, td, J=7.8, 2.3 Hz), 2.95-3.04 (2H, m) ppm. MS (ESI) m/z: 157 (M+H)+

Workup

  1. filtrationFiltered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bdac0d8cded94a97b5783f72c5ed654b
Source dataset
uspto-grants-2015_07
Patent number
US09079929B2

Reaction notes

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