Ceric ammonium nitrate → HCID 42599867, compound

HRID 1898732Notes

Reaction equation

HRID 1898732 reaction equation
[OH:1][C:2]1[C:3]([CH3:21])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:20])([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])[CH2:6][CH2:5]2.[O:22]=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>>[OH:22][C:7]([CH3:20])([CH2:6][CH2:5][C:4]1[C:9](=[O:8])[C:10]([CH3:13])=[C:11]([CH3:12])[C:2](=[O:1])[C:3]=1[CH3:21])[C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15]

Participants

3

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 17840916HCID 17840916, compound

Product 1

HCID 42599867HCID 42599867, compoundYield 73.1%

Procedure

Oxidation as described in protocol B, using 155 mg (0.528 mmol) of 6-hydroxy-N-methoxy-N,2,5,7,8-pentamethylchroman-2-carboxamide and 637 mg CAN (1.16 mmol) yielding 119.4 mg of 2-hydroxy-N-methoxy-N,2-dimethyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid.

Sources & evidence

ORD record
ord-62a5fe34b9c1431e9e6e848cb5a4e019
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

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