Ceric ammonium nitrate → HCID 42598877, compound

HRID 2428233Notes

Reaction equation

HRID 2428233 reaction equation
[OH:1][C:2]1[C:3]([CH3:22])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:21])([C:14]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])=[O:15])[CH2:6][CH2:5]2.[O:23]=[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:23][C:7]([CH3:21])([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[CH3:22])[C:14]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])=[O:15]

Participants

3

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 54096213HCID 54096213, compound

Product 1

HCID 42598877HCID 42598877, compoundYield 83.5%

Procedure

Oxidation as described in protocol B, using 56.7 mg (0.184 mmol) of 6-hydroxy-N-(3-hydroxypropyl)-2,5,7,8-tetramethylchroman-2-carboxamide and 222 mg CAN (0.406 mmol) yielded 49.7 mg of 2-hydroxy-N-(3-hydroxypropyl)-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid.

Sources & evidence

ORD record
ord-a15d22e495b74a3eb309a34f054679ec
Source dataset
uspto-grants-2011_06
Patent number
US07968746B2

Reaction notes

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