Acetic Acid → 3-(1-Methyl-1,2,3,6-tetrahydro-4-pyridyl)-1H-indole-5-carbaldehyde

HRID 128965Notes

Reaction equation

HRID 128965 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#N)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.[PH2]([O-])=[O:20].[Na+].C(O)(=O)C.[NH4+].[OH-]>[Ni].O.N1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:20])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 149732163-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrileHCID 178527019HCID 178527019, compound

Product 1

HCID 152332753-(1-Methyl-1,2,3,6-tetrahydro-4-pyridyl)-1H-indole-5-carbaldehyde

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

Raney nickel (ca 10 g) was added to a solution of the product from step (a) (5.0 g) and sodium hypophosphite (6.0 g) in a mixture of water (25 ml), glac. acetic acid (25 ml) and pyridine (50 ml) at 45° C. The resulting mixture was stirred at 45° C for 1 hour, cooled and basified to pH 9 with 0.88 NH4OH. The mixture was filtered through Hyflo and the filtrate extracted with chloroform. The combined extracts were dried and evaporated in vacuo to give the desired product as an off-white solid which was recrystallised from ethanol (2.4 g).

Workup

  1. customat 45° C
  2. temperaturecooled
  3. filtrationThe mixture was filtered through Hyflo
  4. extractionthe filtrate extracted with chloroform
  5. customThe combined extracts were dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-addd259b282842f7b5d1f4246dbd6f88
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

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