HCID 19045274, compound → HCID 19045276, compound

HRID 1781372Notes

Reaction equation

HRID 1781372 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH2:12][C:11](=[O:13])[C:10]3[CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=[CH:17][C:9]=3[O:8]2)[CH2:4][CH2:3]1>C(O)(=O)C.[Ni]>[NH2:18][C:15]1[CH:16]=[CH:17][C:9]2[O:8][C:5]3([CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[CH2:12][C:11](=[O:13])[C:10]=2[CH:14]=1

Participants

4

Reactant 1

HCID 19045274HCID 19045274, compound

Product 1

HCID 19045276HCID 19045276, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

The 3,4-dihydro-1'-methyl-6-nitro-spiro[2H-1-benzopyran-2,4'-piperdin]-4-one (11.2 g, 0.04 mol) was dissolved in acetic acid (200 ml) and was hydrogenated using two "lab spoon" spatulas of Raney nickel catalyst in a Parr shaker. The theoretical amount of hydrogen was absorbed in 4 hours. The reaction mixture was filtered under nitrogen and the acetic acid was removed in vacuo. The residual oil was taken up in 3N HCl (150 ml), washed with ethyl acetate and neutralized with solid sodium bicarbonate. The product was extracted into ethyl acetate (3×100 ml), washed with sat'd. NaCl, dried, filtered and concentrated in vacuo to yield 7.4 g (75%) of product.

Workup

  1. customThe theoretical amount of hydrogen was absorbed in 4 hours
  2. filtrationThe reaction mixture was filtered under nitrogen
  3. customthe acetic acid was removed in vacuo
  4. washwashed with ethyl acetate and neutralized with solid sodium bicarbonate
  5. extractionThe product was extracted into ethyl acetate (3×100 ml)
  6. washwashed with sat'd
  7. dry with materialNaCl, dried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b71bc264b15d49928dd81de121d205e8
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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