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

HRID 1608976Notes

Reaction equation

HRID 1608976 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-72dfa83820da4f22874e0d91347abe07
Source dataset
uspto-grants-1995_03
Patent number
US05399574

Reaction notes

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