Indole → Indole-3-Carboxaldehyde

HRID 371679Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.P(Cl)(Cl)(Cl)=O.CN([CH:18]=[O:19])C>>[CH:18]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:19]

Participants

Reactant 3

HCID 798Indole

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

Product 1

HCID 10256Indole-3-Carboxaldehyde

Procedure

As shown by the above generalized scheme, the indole is treated with phosphorus oxychloride and DMF to produce the corresponding 3-formyl indole (XIV). The latter is treated with nitromethane and ammonium acetate to obtain the corresponding 3-(2'-nitroethenyl)indole (XV), which then is reduced to the desired tryptamine (XVI).

Sources & evidence

ORD record: ord-132f02bc76474e77bae2d8221eba4292
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04087444

Reaction notes

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