Methanol → HCID 68292906, compound

HRID 1504973Notes

Reaction equation

HRID 1504973 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=1.[Mn]([O-])(=O)(=O)=O.[K+].CO>C(#N)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 516875Potassium PermanganateHCID 68292861HCID 68292861, compound

Product 1

HCID 68292906HCID 68292906, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 132 (400 mg, 1.71 mmol) was first dissolved in acetonitrile (20 mL), with potassium permanganate (952 mg, 5.13 mmol) and alumina (1.2 g) added into the solution in batch. After stirring the resulting mixture at room temperature for 40 min, CH3OH (1 mL) was added to reduce excess oxidant. The mixture was then filtered and the solid material was washed with DCM:CH3OH=10:1. The filtrate was concentrated, and purified with silica gel column chromatography (EtOAc:TEA=1:0.1) to give compound 133 (110 mg, 30%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ9.32-9.37 (m, 1H), 8.37-8.42 (m, 1H), 7.35-7.41 (m, 1H), 6.97 (br s, 2H), 2.98 (t, 2H, J=7.2 Hz), 2.78 (d, 2H, J=7.2 Hz), 2.17-2.26 (m, 2H).

Workup

  1. additionadded into the solution in batch
  2. filtrationThe mixture was then filtered
  3. washthe solid material was washed with DCM
  4. concentrationThe filtrate was concentrated
  5. custompurified with silica gel column chromatography (EtOAc:TEA=1:0.1)

Sources & evidence

ORD record
ord-0803957e60f845e196868a4cdec28ec7
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

Loading…