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

HRID 1975764Notes

Reaction equation

HRID 1975764 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 CH2Cl2CH3OH (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 CH2Cl2CH3OH (19:1) as eluant

Sources & evidence

ORD record
ord-3abe83edc7584468a3b2a394556ddf15
Source dataset
uspto-grants-1994_02
Patent number
US05288748

Reaction notes

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