7-Hydroxycyclindole → 3-(Dimethylamino)-7-hydroxy-1,2,3,4-tetrahydrocarbazole

HRID 1077369Notes

Reaction equation

HRID 1077369 reaction equation
Cl.[CH3:2][N:3]([CH3:25])[CH:4]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([O:17]CC4C=CC=CC=4)=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH2:6][CH2:5]1.Cl.CN(C)C1CC2C3C(=CC(O)=CC=3)NC=2CC1>[Pd].C(O)C>[CH3:2][N:3]([CH3:25])[CH:4]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][C:11]([OH:17])=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 30851017-HydroxycyclindoleHCID 23470234HCID 23470234, compound

Product 1

HCID 30851023-(Dimethylamino)-7-hydroxy-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following a procedure similar to that described in Example 258 and using 12 g. of 3-(dimethylamino)-7-benzyloxy-1,2,3,4-tetrahydrocarbazole hydrochloride (Example 239) in 200 ml. of aqueous ethyl alcohol (1:1) and 2 g. of 10% palladium on charcoal, there was obtained 10 g. of 3-(dimethylamino)-7-hydroxy-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 286°-288°C.

Sources & evidence

ORD record
ord-9a4d0ac9b61d4c118edafb6b3de00c13
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

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