HCID 67391750, compound → HCID 86657620, compound

HRID 1617411Notes

Reaction equation

HRID 1617411 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:3]>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH:15]=[O:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:3]

Participants

4

Reactant 1

HCID 67391750HCID 67391750, compound

Product 1

HCID 86657620HCID 86657620, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

Manganese(IV) oxide (0.72 g, 8.3 mmol) was added to methyl 3-[(dimethylamino)methyl]-5-(hydroxymethyl)benzoate (0.37 g, 1.6 mmol, from Step A) in Toluene (15 mL). The mixture was heated to 105° C. for 2 hours, then was cooled to room temperature and filtered. Solvent was removed from the filtrate in vacuo to afford the product as a colorless oil. Yield: 0.30 g (82%); LC-MS: 222.1 (M+H)+. 1H NMR (400 MHz, CDCl3): δ 10.07 (s, 1H), 8.43 (dd, 1H), 8.25 (dd, 1H), 8.05 (dd, 1H), 3.96 (s, 3H), 3.54 (s, 2H), 2.26 (s, 6H).

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationfiltered
  3. customSolvent was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-341eafc2a04a480092bdc3ec9fac1be9
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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