Ceric ammonium nitrate → HCID 42599869, compound

HRID 2428285Notes

Reaction equation

HRID 2428285 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][NH:5][C:6]([C:8]1([CH3:22])[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([CH3:21])[C:12]([CH3:20])=[C:13]([OH:19])[C:14]=2[CH3:18])[O:9]1)=[O:7].[O:24]=[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+].C([O-])(O)=O.[Na+]>>[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][NH:5][C:6](=[O:7])[C:8]([OH:24])([CH3:22])[CH2:17][CH2:16][C:15]1[C:10](=[O:9])[C:11]([CH3:21])=[C:12]([CH3:20])[C:13](=[O:19])[C:14]=1[CH3:18]

Participants

4

Reactant 3

HCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 11723535HCID 11723535, compound

Product 1

HCID 42599869HCID 42599869, compoundYield 83.2%

Procedure

Oxidation as described in protocol B, using 150 mg N-(2-(dimethylamino)-ethyl)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide (0.468 mmol) and 564 mg CAN (1.03 mmol) with exceptions as noted. The aqueous phase was basified with NaHCO3 (s), extracted with EtOAc and the combined organics dried with Na2SO4, concentrated and flashed yielding 131 mg (83%) of N-(2-(dimethylamino)-ethyl)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe combined organics dried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f1d4815f465c4cf2b2c5e615dbe773cc
Source dataset
uspto-grants-2011_06
Patent number
US07968746B2

Reaction notes

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