m-Chloroperbenzoic acid → HCID 178479968, compound

HRID 511554Notes

Reaction equation

HRID 511554 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:12])[N:9]([CH3:11])[CH2:10][C:6]=2[CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:21])C=1>CC(C)=O>[NH2:1][C:2]1[C:7]2[C:8](=[O:12])[N:9]([CH3:11])[CH2:10][C:6]=2[CH:5]=[CH:4][N+:3]=1[O-:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 672535394-amino-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one2×

Product 1

HCID 178479968HCID 178479968, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-amino-2-methyl-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one (Compound 3108, 62.5 mg, 0.383 mmol) and m-Chloroperbenzoic acid (145 mg, 0.843 mmol) in Acetone (10.0 mL) was stirred at rt for 90 minutes. The reaction mixture was concentrated under reduced pressure to an off white solid. The crude material was purified by silica gel chromatography on the combi-flash Rf system using DCM/7 N NH3 in MeOH (100:0→90:10) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a white solid (68.3 mg, 99.5%). 1H NMR (DMSO-d6, 400 MHz): δ=8.19 (d, J=6.57 Hz, 1H), 7.02 (br. s., 2H), 6.82 (d, J=6.57 Hz, 1H), 4.41 (s, 2H), 3.01 (s, 3H). MS (ES+): m/z 180.07 [MH+] (TOF, polar).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to an off white solid
  2. customThe crude material was purified by silica gel chromatography on the combi-flash Rf system
  3. additionThe fractions containing product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-600c9f62e08349149923aa25f65a5772
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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