6-nitro-3-(N-propionyl-N-n-propylamino)chroman → 6-amino-3-(N-propionyl-N-n-propylamino)chroman

HRID 266167Notes

Reaction equation

HRID 266167 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH:8]([N:14]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[CH2:7]2)([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][CH:8]([N:14]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[CH2:7]2

Participants

4

Reactant 1

HCID 108511876-nitro-3-(N-propionyl-N-n-propylamino)chroman

Product 1

HCID 105634506-amino-3-(N-propionyl-N-n-propylamino)chromanYield 56%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 6-nitro-3-(N-propionyl-N-n-propylamino)chroman (17) (700 mg, 2.40 mmol) in glacial acetic acid (50 ml) was treated with zinc dust (1.0 g). The mixture was stirred at 50° C. for 90 minutes. The solution was filtered and acetic acid evaporated at reduced pressure. The product was dissolved in CH2Cl2 and washed with 5% -aqueous Na2CO3. The organic layer was separated, dried (Na2SO4) and the solvent was evaporated. The crude product was chromatographed on silica (60 g) , with CH2Cl2 --CH3OH (19:1) as eluant, yielding 350 mg (56%) of 6-amino-3-(N-propionyl-N-n-propylamino)chroman (18) as an oil.

Workup

  1. filtrationThe solution was filtered
  2. customacetic acid evaporated at reduced pressure
  3. dissolutionThe product was dissolved in CH2Cl2
  4. washwashed with 5% -aqueous Na2CO3
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was evaporated
  8. customThe crude product was chromatographed on silica (60 g) , with CH2Cl2 --CH3OH (19:1) as eluant

Sources & evidence

ORD record
ord-979ee10d9c834d38a381495c6bf9e458
Source dataset
uspto-grants-1997_07
Patent number
US05650427

Reaction notes

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