HCID 86725136, compound → HCID 86725137, compound

HRID 2204928Notes

Reaction equation

HRID 2204928 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:43]=[C:44]([N+:46]([O-])=O)[CH:45]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[C:29](/[C:32]2[CH:40]=[CH:39][C:35]3[O:36][CH2:37][O:38][C:34]=3[CH:33]=2)\[C:30]#[N:31])=[CH:24][C:23]=1[O:41][CH3:42])=[O:8])([O-])=O>CN(C=O)C.O.[Zn]>[NH2:46][C:44]1[CH:43]=[C:6]([CH:5]=[C:4]([NH2:1])[CH:45]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[C:29](/[C:32]2[CH:40]=[CH:39][C:35]3[O:36][CH2:37][O:38][C:34]=3[CH:33]=2)\[C:30]#[N:31])=[CH:24][C:23]=1[O:41][CH3:42])=[O:8]

Participants

5

Reactant 1

HCID 86725136HCID 86725136, compound

Product 1

HCID 86725137HCID 86725137, compoundYield 61.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5 g (7.6 mmol) of 11-{4-[(Z)-2-(1,3-benzodioxol-5-yl)-2-cyanoethenyl]-2-methoxyphenoxy}undecyl 3,5-dinitrobenzoate are dissolved in a mixture of 84 ml of DMF and 9 ml of water. 15.7 g (58 mmol) of ferric chloride hexahydrate are added. 6.31 g (97 mmol) of zinc powder are added portionwise within 30 min. The mixture is allowed to react for 2 hours. The reaction mixture is then partitioned between ethyl acetate and water and filtered. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. Filtration of the residue on silica gel using toluene:ethyl acetate(1:3) as eluant and yielded 2.8 g (61%) of 11-{4-[(Z)-2-(1,3-benzodioxol-5-yl)-2-cyanoethenyl]-2-methoxyphenoxy}undecyl 3,5-diaminobenzoate as a white powder.

Workup

  1. customto react for 2 hours
  2. customThe reaction mixture is then partitioned between ethyl acetate and water
  3. filtrationfiltered
  4. washThe organic phase is washed repeatedly with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. filtrationFiltration of the residue on silica gel

Sources & evidence

ORD record
ord-aeca99bf3a49499d90215a2c1316bc20
Source dataset
uspto-grants-2016_06
Patent number
US09366906B2

Reaction notes

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