Acetic Acid → 3-(1,6-Dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]-indol-3-yl)benzaldehyde

HRID 133187Notes

Reaction equation

HRID 133187 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:22](=[O:23])[N:21]([CH3:24])[C:12]3[NH:13][C:14]4[C:19]([C:11]=3[CH:10]=2)=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=4)[CH:6]=[CH:7][CH:8]=1)#N.CC(O)=[O:27].[PH2]([O-])=O.[Na+]>[Ni].N1C=CC=CC=1>[CH3:24][N:21]1[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH:10]=[C:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH:1]=[O:27])[C:22]1=[O:23])=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 673879473-(3-cyanophenyl)-1,6-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-oneHCID 178527019HCID 178527019, compound

Product 1

HCID 866023433-(1,6-Dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]-indol-3-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

450 mg of 3-(3-cyanophenyl)-1,6-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one, 10 ml of AcOH, 20 ml of pyridine, 2.6 g of sodium hypophosphite and 434 mg of Raney Ni are mixed and then the mixture is heated at 60° C. for 4 hours. The reaction medium is filtered and the filtrate is evaporated; the residue is taken up in 50 ml of AcOEt/CH2Cl2 (1/1; v/v) and the organic phase is washed with water, dried and evaporated to produce the expected compound, M.p.=280° C.

Workup

  1. filtrationThe reaction medium is filtered
  2. customthe filtrate is evaporated
  3. washthe organic phase is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-b9d5a5ddf3364bd3be98a2eec401b06b
Source dataset
uspto-grants-2008_06
Patent number
US07390818B2

Reaction notes

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