Water → N'-hydroxy-6-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboximidamide

HRID 873523Notes

Reaction equation

HRID 873523 reaction equation
[C:1](=O)([O-])[O-].[Na+].[Na+].CO[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[CH:23]1[C:36]2[C:35](=[O:37])[CH2:34][C:33]([CH3:39])([CH3:38])[CH2:32][C:31]=2[O:30][C:29]2[CH2:28][C:27]([CH3:41])([CH3:40])[CH2:26][C:25](=[O:42])[C:24]1=2.Cl.[NH2:44][OH:45].[OH2:46]>CO>[OH:45][N:44]=[C:21]([C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:46][CH3:1])=[C:10]([CH:23]3[C:24]4[C:25](=[O:42])[CH2:26][C:27]([CH3:41])([CH3:40])[CH2:28][C:29]=4[O:30][C:31]4[CH2:32][C:33]([CH3:39])([CH3:38])[CH2:34][C:35](=[O:37])[C:36]3=4)[CH:11]=2)[N:20]=1)[NH2:22]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 117700637HCID 117700637, compound

Product 1

HCID 137187592N'-hydroxy-6-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboximidamideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium carbonate (122 mg, 1.15 mmol) was added to a suspension of the 6-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carbonitrile produced in Example 6 (410 mg, 0.85 mmol) and hydroxylamine hydrochloride (73.8 mg, 1.06 mmol) in methanol (8.2 ml) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 25 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with dichloromethane. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure to obtain the title compound (429 mg, yield: 98%).

Workup

  1. customthe mixture thus obtained
  2. extractionthe mixed solution was then extracted with dichloromethane
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-e6074b1146a3475c89d57598eff5753d
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

Loading…