3-(Dimethylamino)-6-nitro-1,2,3,4-tetrahydrocarbazole → 6-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole

HRID 461548Notes

Reaction equation

HRID 461548 reaction equation
[CH3:1][N:2]([CH3:19])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:16]([O-])=O)[CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1.[H][H]>[Ni].C(O)C>[CH3:1][N:2]([CH3:19])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH2:16])[CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 128917803-(Dimethylamino)-6-nitro-1,2,3,4-tetrahydrocarbazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 226115606-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

3-(Dimethylamino)-6-amino-1,2,3,4-tetrahydrocarbazole is prepared by dissolving 0.1 mole of 3-(dimethylamino)-6-nitro1,2,3,4-tetrahydrocarbazole (Example 10) in 400 ml. absolute ethyl alcohol and hydrogenating over Raney nickel at about 350 psig and at room temperature until the required amount of hydrogen has reacted. The resulting 3-(dimethylamino)-6-amino-1,2,3,4-tetrahydrocarbazole can be isolated and purified using conventional procedures.

Workup

  1. custom3-(Dimethylamino)-6-amino-1,2,3,4-tetrahydrocarbazole is prepared

Sources & evidence

ORD record
ord-faab26906abc4ea9975bdca16361c05b
Source dataset
uspto-grants-1977_12
Patent number
US04062864

Reaction notes

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