2-(1-benzyl-3-hydroxy-5-hydroxy-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide → 2-(1-Benzyl-5-formyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide

HRID 71045Notes

Reaction equation

HRID 71045 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=C(C)C(O)=[CH:14][CH:15]=2)[C:10]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])([OH:19])[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].ClCCl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:16][C:11]([CH:10]=[O:19])=[CH:14][CH:15]=2)[C:10]([CH2:20][C:21]([N:23]([CH3:24])[CH3:25])=[O:22])([OH:19])[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 671482252-(1-benzyl-3-hydroxy-5-hydroxy-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide

Product 1

HCID 117255532-(1-Benzyl-5-formyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamideYield 198.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Under inert atmosphere, a flask is charged with manganese dioxide (8.7 g, 0.1 mop and 2-(1-benzyl-3-hydroxy-5-hydroxy-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide (Example 23) (3.54 g, 0.01 mol). To this, mol sieve (4 A, 2 g) and dichloromethane (100 mL) are added, and the mixture is heated under reflux for six hours. The mixture is then filtered, and evaporation of the solvent leaves 3.5 g of a dark brown foam. This is chromatographed on silica (ethyl acetate) to give 1.8 g (50%) of the title product as pale yellow foam. 1H-NMR (CDCl3, 300 MHz) δ 2.82, 3.13 (AB, 2H, 2J=16.1Hz, CH2NMe2); 2.95, 2.98 (2 s, 3H each, N(CH3)2); 4.93, 4.94 (AB, 2H, 2J=16 Hz, NCH2Ph); 6.11 (s, 1H, OH); 6.82 (d, 1H, 3J=7.9 Hz, H-7); 7.23-7.38 (m, 5H, Ph); 7.72 (dd, 1H, 4J=1.5 Hz, H-6); 8.00 (d, 1H, H-4); 9.83 (s, 1H, CHO). 13C-NMR (CDCl3, 75 MHz) δ 35.76, 37.70 (N(CH3)2); 38.72 (CH2CONMe2); 44.42 (NCH2Ph); 74.06 (C-3); 109.80 (C-7); 125.38 (C-4); 127.42 (Bn ortho-C); 128.14 (Bn para-C); 129.16 (Bn meta-C); 132.00, 132.31 (C-5, C-9); 133.49 (C-6); 135.04 (Ph ipso-C); 148.24 (C-8); 170.22 (CONMe2); 176.69 (C-2); 190.80 (CHO).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for six hours
  3. filtrationThe mixture is then filtered
  4. customevaporation of the solvent

Sources & evidence

ORD record
ord-ba7b75592aee46b39465ab60ec81cc11
Source dataset
uspto-grants-2014_09
Patent number
US08822702B2

Reaction notes

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