HCID 59164513, compound → HCID 59164427, compound

HRID 1894098Notes

Reaction equation

HRID 1894098 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14]>C(Cl)Cl.O=[Mn]=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:15])[CH3:14]

Participants

4

Reactant 1

HCID 59164513HCID 59164513, compound

Product 1

HCID 59164427HCID 59164427, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-acetylamino-4-hydroxymethyl-benzoic acid methyl ester (1.7 g, 7.62 mmol) in DCM (40 mL) was added MnO2 (1.32 g, 2 equiv) and the resulting mixture was stirred at 50° C. for 18 h. MnO2 (0.66 g, 1 equiv) was added and the mixture was stirred at 50° C. for 2 h. The mixture was cooled down, filtered through a pad of celite and washed with DCM. The solvent was removed in vacuo to afford a crude yellow solid. The residue was purified by flash chromatography (silica gel, EtOAc/hexanes (0:100 to 50:50)) to provide the title compound as a light yellow solid (1.15 g, 68%) (ES-MS: m/z 263.2 [M+CH3CN+H]+, rt 4.29 min).

Workup

  1. stirringthe mixture was stirred at 50° C. for 2 h
  2. temperatureThe mixture was cooled down
  3. filtrationfiltered through a pad of celite
  4. washwashed with DCM
  5. customThe solvent was removed in vacuo
  6. customto afford a crude yellow solid
  7. customThe residue was purified by flash chromatography (silica gel, EtOAc/hexanes (0:100 to 50:50))

Sources & evidence

ORD record
ord-9b8439610aa8412194ac8e721789962b
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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