Methanol → HCID 86689305, compound

HRID 1852490Notes

Reaction equation

HRID 1852490 reaction equation
CO.[N+:3]([C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[CH:8][C:7]=1[NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21])([O-])=O>[Pt]=O.O1CCCC1>[NH2:3][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[CH:8][C:7]=1[NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21]

Participants

5

Reactant 2

HCID 887MethanolHCID 86689303HCID 86689303, compound

Product 1

HCID 86689305HCID 86689305, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a methanol (10 mL) and anhydrous tetrahydrofuran (30 mL) solution of 3-(1-nitro-5,6,7,8-tetrahydronaphthalen-2-ylamino)benzonitrile (1.52 g, 5.17 mmol was added platinum oxide (50 mg), and the mixture was hydrogenated for 29 hours at room temperature under atmospheric pressure. After removal of the catalyst by filtration, the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give the titled compound as yellow powder (747 mg, yield 55%).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-12c99166296345fdb8f3e821158a6d2f
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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