HCID 67148438, compound → HCID 86632364, compound

HRID 2428144Notes

Reaction equation

HRID 2428144 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][CH3:13])=[O:11])=[CH:4][C:3]=1[CH2:14][OH:15]>CC#N.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][CH3:13])=[O:11])=[CH:4][C:3]=1[CH:14]=[O:15]

Participants

4

Reactant 1

HCID 67148438HCID 67148438, compound

Product 1

HCID 86632364HCID 86632364, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6342AcetonitrileSolvent

Procedure

MnO2 (10.6 g, 110 mmol) was added to a sol. of 3-(4-chloro-3-hydroxymethyl-phenyl)-N-methyl-propionamide (2.50 g, 11.0 mmol) in CH3CN (223 mL). The mixture was stirred for 1 h at rt. The mixture was filtered over celite and washed with CH3CN and CH2Cl2. The filtrate was evaporated under reduced pressure, and the residue was dried under high vacuum to yield the crude title compound (2.30 g, 93%) that was used without further purification. LC-MS: tR=0.76 min; ES+: 267.30.

Workup

  1. filtrationThe mixture was filtered over celite
  2. washwashed with CH3CN and CH2Cl2
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-17a656253a8f473aa427c1ea26e8b1df
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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