Ammonia → 4-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbonitrile

HRID 1711223Notes

Reaction equation

HRID 1711223 reaction equation
[O:1]=[C:2]1[C:11]2[O:12][C:13]([CH:15]=O)=[CH:14][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:4]=2[NH:3]1.[NH3:23]>C(O)(C)C.O=[Mn]=O>[O:1]=[C:2]1[C:11]2[O:12][C:13]([C:15]#[N:23])=[CH:14][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:4]=2[NH:3]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 597967754-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbaldehyde

Product 1

HCID 247583904-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 4-oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbaldehyde (v) in isopropanol (“iPrOH”) is treated with ammonia gas at room temperature. After 90 min, the reaction is treated with MnO2 and stirred for an additional 16 h. The reaction is filtered and evaporated onto celite. Chromatography on silica gel affords 4-oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbonitrile.

Workup

  1. filtrationThe reaction is filtered
  2. customevaporated onto celite

Sources & evidence

ORD record
ord-f5f842a8051f425cbbbeec3045e401a8
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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