HCID 117892035, compound → HCID 90161013, compound

HRID 930543Notes

Reaction equation

HRID 930543 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:21]([O-])=O)=[C:11]([CH:20]=2)[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:3][CH2:2]1.[H][H]>C1COCC1.[Ni]>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:20]=[C:11]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[C:10]([NH2:21])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 117892035HCID 117892035, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90161013HCID 90161013, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-(3,6-dihydro-2H-pyran-4-yl)-2-nitro-N-(pyridin-2-ylmethyl)aniline E-1.9′ (82 mg; 0.26 mmol) is dissolved in THF (25 ml) and filled into a Büchi autoclave. RaNi is added and the reaction is hydrogenated with 5 bar hydrogen pressure overnight. The reaction mixture is filtered on a plug of celite. The filtrate is then concentrated under reduced pressure. The product is used in the next step without further purification.

Workup

  1. additionfilled into a Büchi autoclave
  2. filtrationThe reaction mixture is filtered on a plug of celite
  3. concentrationThe filtrate is then concentrated under reduced pressure
  4. customThe product is used in the next step without further purification

Sources & evidence

ORD record
ord-ffefc598bef34aeaa7cf4009a214df3d
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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