Tryptamine → 1-hydroxyindole

HRID 1798018Notes

Reaction equation

HRID 1798018 reaction equation
NCC[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C1C([OH:19])=CC2C(CCN)=CNC=2C=1.CNCCC1C2C=C(O)C=CC=2NC=1.COC1C=C2C(NC=C2CCNC)=CC=1>>[OH:19][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

5

Reactant 4

HCID 1150TryptamineHCID 5202SerotoninHCID 161845-Methoxy-N-methyl-1H-indole-3-ethanamineHCID 150885N-Methylserotonin

Product 1

HCID 108879551-hydroxyindole

Procedure

1-hydroxyindole can be prepared in 2 stages from indole by reducing it to triethylsilane in trifluoroacetic acid then by treating the indoline obtained with an aqueous solution of H2O2 (30%) in the presence of a catalytic quantity (20%) of sodium tungstate dihydrate (Na2WO4.H2O) in methanol at 0° C. according to a procedure described in M. Somei, F. Yamada, T. Kurauchi, Y. Nagahama, M. Hasegawa, K. Yamada, S. Teranishi, H. Sato, C. Kaneko Chem. Pharm. Bull. 2001, 49, 87-96. This procedure was used in the preparation, from tryptamine derivatives, of several compounds oxygenated in position 5 of the indole ring such as for example serotonin, the N-methylserotonin and 5-methoxy-N-methyltryptamine.

Sources & evidence

ORD record
ord-f3e3f336fd3e4ad4903f7d10ab3c110f
Source dataset
uspto-grants-2013_01
Patent number
US08343964B2

Reaction notes

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