HCID 178476666, compound → HCID 178476664, compound

HRID 353693Notes

Reaction equation

HRID 353693 reaction equation
[Br-:1].[CH3:2][N:3]([CH3:39])[C:4]1[CH:5]=[CH:6][C:7]2[C:16]([CH:17]=1)=[O+:15][C:14]1[C:9](=[CH:10][CH:11]=[C:12]([N:18]([CH3:20])[CH3:19])[CH:13]=1)[C:8]=2[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[C:23]([NH2:30])[C:22]=1[C:31]([O:33][CH2:34][O:35][C:36](=[O:38])[CH3:37])=[O:32]>C(O)C.ClCCl.[Pd]>[Br-:1].[CH3:20][N:18]([CH3:19])[C:12]1[CH:11]=[CH:10][C:9]2[C:14]([CH:13]=1)=[O+:15][C:16]1[C:7](=[CH:6][CH:5]=[C:4]([N:3]([CH3:2])[CH3:39])[CH:17]=1)[C:8]=2[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([NH2:30])[C:22]=1[C:31]([O:33][CH2:34][O:35][C:36](=[O:38])[CH3:37])=[O:32]

Participants

5

Reactant 1

HCID 178476666HCID 178476666, compound

Product 1

HCID 178476664HCID 178476664, compoundYield 50.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The aforementioned 3,6-bis(dimethylamino)-9-(2-acetoxymethoxycarbonyl-3-amino-4-nitrophenyl)xanthylium bromide (443 mg) was dissolved in a mixed solvent of ethanol (100 ml) and dichloromethane (100 ml), and the solution was added with 0.25 g of 10% Pd/C catalyst. The mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The reaction mixture was filtered, and the solvent was evaporated. The residue was purified by silica gel column chromatography to obtain 3,6-bis(dimethylamino)-9-(2-acetoxymethoxycarbonyl-3,4-diaminophenyl)xanthylium bromide (214 mg, 50.9%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-23e2ea2626724cf59536de83a56a59ce
Source dataset
uspto-grants-2004_06
Patent number
US06756231B1

Reaction notes

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