HCID 86732646, compound → HCID 20719184, compound

HRID 523322Notes

Reaction equation

HRID 523322 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:31]=[C:32]([N+:34]([O-])=O)[CH:33]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([O:27][CH3:28])=[O:26])=[CH:19][C:18]=1[O:29][CH3:30])=[O:8])([O-])=O>CN(C=O)C.O.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:31]=[C:32]([NH2:34])[CH:33]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([O:27][CH3:28])=[O:26])=[CH:19][C:18]=1[O:29][CH3:30])=[O:8]

Participants

5

Reactant 1

HCID 86732646HCID 86732646, compound

Product 1

HCID 20719184HCID 20719184, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5 g (9.7 mmol) of 6-{2-methoxy-4-[(1E)-3-methoxy-3-oxoprop-1-enyl]phenoxy}hexyl 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 2.7 g (61%) of 6-{2-methoxy-4-[(1E)-3-methoxy-3-oxoprop-1-enyl]phenoxy}hexyl 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-518a04f206f347239db68a54c5b1036d
Source dataset
uspto-grants-2016_05
Patent number
US09334366B2

Reaction notes

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