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Methanol → 5-Fluoro-N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

HRID 1077358
Notes
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Reaction equation

HRID 1077358 reaction equation
[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[C:9](Br)[CH:10]=[CH:11][C:12]=3[F:16])[NH:7][C:6]=2[CH2:5][CH2:4]1.CO.[OH-].[K+]>[Pd].O>[CH3:1][N:2]([CH3:18])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[F:16])[NH:7][C:6]=2[CH2:5][CH2:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 12891793HCID 12891793, compound

Product 1

HCID 123618445-Fluoro-N,N-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962Water
Solvent

Procedure

Following a procedure similar to that described in Example 234 but using 2 g. of 3-(dimethylamino)-8-bromo-5-fluoro-1,2,3,4-tetrahydrocarbazole (Example 219), in 100 ml. of methyl alcohol, 1 g. of 10% palladium on charcoal and 1 g. of potassium hydroxide in 2 ml. of water there was obtained, after recrystallization from benzene, 1.3 g. of 3-(dimethylamino)-5-fluoro-1,2,3,4-tetrahydrocarbazole, m.p. 166°-168°C.

Workup

  1. customafter recrystallization from benzene, 1.3 g

Sources & evidence

ORD record
ord-8c2c2fdc6e5d4f4a92a2f8607346d337
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03959309

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes