Ceric ammonium nitrate → HCID 42599870, compound

HRID 1755595Notes

Reaction equation

HRID 1755595 reaction equation
[OH:1][C:2]1[C:3]([CH3:27])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:26])([C:14]([NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)=[O:15])[CH2:6][CH2:5]2.[O:28]=[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:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][NH:16][C:14](=[O:15])[C:7]([OH:28])([CH3:26])[CH2:6][CH2:5][C:4]2[C:9](=[O:8])[C:10]([CH3:13])=[C:11]([CH3:12])[C:2](=[O:1])[C:3]=2[CH3:27])=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 67263027HCID 67263027, compound

Product 1

HCID 42599870HCID 42599870, compoundYield 14.4%

Procedure

Oxidation as described in protocol B, using 100 mg 6-hydroxy-N-(4-hydroxyphenethyl)-2,5,7,8-tetramethylchroman-2-carboxamide (0.271 mmol) and 325 mg CAN (0.595 mmol) yielded 15 mg of N-(4-hydroxyphenethyl)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid.

Sources & evidence

ORD record
ord-4d26c630bad14f1f95e42c9c08cb02f2
Source dataset
uspto-grants-2015_10
Patent number
US09169196B2

Reaction notes

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