Dimethylformamide → HCID 19353254, compound

HRID 378251Notes

Reaction equation

HRID 378251 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3C=C4[C:24](=[C:25]([C:31](OC)=[O:32])[C:26]=3[CH2:27][CH2:28][C:29]#[N:30])C35OCOC3C=CC=C5C=C4)=[CH:9][C:4]=2[O:3][CH2:2]1.CN([CH:38]=[O:39])C>[Ni]>[NH2:30][CH2:29][CH2:28][CH2:27][C:26]1[C:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)=[C:6]2[C:7]([CH:8]=[CH:9][C:4]3[O:3][CH2:2][O:1][C:5]=32)=[CH:24][C:25]=1[C:31]([O:39][CH3:38])=[O:32]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 70270777HCID 70270777, compound

Product 1

HCID 19353254HCID 19353254, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a DMF (1 ml) solution of methyl 9-(1,3-benzodioxol-5-yl)-8-(2-cyanoethyl)-naphtho[1,2-d]-1,3-benzodioxole-7-carboxylate (21 mg) was added Raney nickel (about 200 mg) and stirred for 6 hours under hydrogen atmosphere. The catalist was filtered off and the reaction mixture was concentrated under reduced pressure, and the obtained residue was purified with column chromatography (silica gel 1 g, eluent:dichloromethane-methanol concentrated NH4OH=15:1:0.1) to give the entitled compound (11 mg).

Workup

  1. filtrationThe catalist was filtered off
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified with column chromatography (silica gel 1 g, eluent:dichloromethane-methanol concentrated NH4OH=15:1:0.1)

Sources & evidence

ORD record
ord-1d887c51fb07476e8f27b9be1710b866
Source dataset
uspto-grants-2000_02
Patent number
US06030967

Reaction notes

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