Methanol → HCID 68293026, compound

HRID 1504971Notes

Reaction equation

HRID 1504971 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][CH2:13][C:14]1[NH:15][CH2:16][CH2:17][N:18]=1.[Mn]([O-])(=O)(=O)=O.[K+].CO>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][CH2:13][C:14]1[NH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 516875Potassium PermanganateHCID 68292979HCID 68292979, compound

Product 1

HCID 68293026HCID 68293026, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 121 (888 mg, 3.53 mmol) was first dissolved in acetonitrile (100 mL), with potassium permanganate (1.12 g, 7.07 mmol) and alumina (4.9 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 evaporated to dryness to give the compound 122 (600 mg, 68%) as a light yellow oil. The crude product was used directly for the next step without purification. 1H NMR (400 MHz, CDCl3) δ7.94-7.99 (m, 1H), 7.85-7.91 (m, 1H), 7.35-7.41 (m, 1H), 6.96 (br s, 2H), 2.75-2.85 (m, 4H), 2.06-2.19 (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. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2de54e0112a34c01aabf6274298824d2
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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