Acetic Acid → Indole-5-carboxaldehyde

HRID 128970

Reaction equation

HRID 128970 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#N.[PH2]([O-])=[O:13].[Na+].C(O)(=O)C.N1C=CC=CC=1>[Ni].O>[NH:8]1[C:9]2[C:5](=[CH:4][C:3]([CH:1]=[O:13])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 27513Indole-5-carbonitrileHCID 178527019HCID 178527019, compound

Product 1

HCID 589040Indole-5-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

Raney nickel (6.7 g) was added to a solution of 5-cyanoindole (Aldrich, 10.0 g) and sodium hypophosphite (20.0 g) in a mixture of water (73 ml), glac. acetic acid (73 ml) and pyridine (145 ml) at 45° C. The resulting mixture was stirred at 45° C. for 2 hours, then cooled and filtered through Hyflo. The filtrate was diluted with water and extracted with ethyl acetate. The combined extracts were washed with water, 10% aqu. citric acid. IN aqu. HCl, water and brine, dried and evaporated in vacuo to give the desired product as a buff solid which was recrystallised from chloroform (7.5 g).

Workup

  1. customat 45° C
  2. temperaturecooled
  3. filtrationfiltered through Hyflo
  4. additionThe filtrate was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined extracts were washed with water, 10% aqu
  7. dry with materialHCl, water and brine, dried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-e9de3552b8cd4484b0aa759ba09f08c1
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Linked notes

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