1,2-Dimethoxyethane → HCID 24880045, compound

HRID 1191976Notes

Reaction equation

HRID 1191976 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]2[C:7]([C:10]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)=[O:11])=[CH:8][O:9][C:5]=2[C:4]=1[N+:26]([O-])=O.C([O-])=O.[NH4+].COCCOC>[Pd].CO>[NH2:26][C:4]1[C:5]2[O:9][CH:8]=[C:7]([C:10]([C:12]3[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=3)=[O:11])[C:6]=2[CH:24]=[CH:25][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 2723923Ammonium formateHCID 59138495HCID 59138495, compound

Product 1

HCID 24880045HCID 24880045, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.022 g (0.057 mmol) of (6-methoxy-7-nitrobenzofuran-3-yl)(3,4,5-trimethoxyphenyl)methanone, 0.1 g of ammonium formate and 0.1 g of 10% palladium on carbon in 5 ml of a mixture of 1,2-dimethoxyethane and methanol (4:1) was refluxed for 30 minutes (TLC controlled reaction). After cooling to room temperature the mixture was filtered through a pad of Celite and washed with methylene chloride. The filtrates were evaporated to dryness under reduced pressure and the residue was purified by flash column chromatography to give 0.011 g (55% yield) of pure title compound as a colorless solid; 1H NMR (CDCl3) δ 3.89 (s, 6H, OMe); 3.92 (s, 6H, OMe); 4.01 (broad s, 2H, NH2); 6.95 (d, 1H, CH aromatic, J=8.54 Hz); 7.14 (s, 2H, CH aromatic); 7.46 (d, 1H, CH aromatic, J=8.54 Hz); 8.0 (s, 1H, CH furan).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. custom(TLC controlled reaction)
  3. filtrationwas filtered through a pad of Celite
  4. washwashed with methylene chloride
  5. customThe filtrates were evaporated to dryness under reduced pressure
  6. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-47ccc168e4eb4d44ad1ece6d595e289e
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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