Ethanol → 2,3,4,9-tetrahydro-1H-carbazol-6-amine

HRID 1991710Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]2=1)([O-])=O.C(O)C.O.O.[Sn](Cl)Cl>C(=O)(O)[O-].[Na+]>[CH2:11]1[C:12]2[NH:13][C:14]3[C:6](=[CH:5][C:4]([NH2:1])=[CH:16][CH:15]=3)[C:7]=2[CH2:8][CH2:9][CH2:10]1

Participants

Conditions

Temperature: 70 °C

Procedure

6-Nitro-2,3,4,9-tetrahydro-1H-carbazole (0.100 g, 0.462 mmol) was dissolved in a 40 mL scintillation vial containing a magnetic stir bar and 2 mL of ethanol. Tin(II) chloride dihydrate (1.04 g, 4.62 mmol) was added to the reaction mixture and the resulting suspension was heated at 70° C. for 16 h. The crude reaction mixture was then diluted with 15 mL of a saturated aqueous solution of sodium bicarbonate and extracted three times with an equivalent volume of ethyl acetate. The ethyl acetate extracts were combined, dried over sodium sulfate, and evaporated to dryness to yield 2,3,4,9-tetrahydro-1H-carbazol-6-amine (82 mg, 95%) which was used without further purification.

Workup

additioncontaining a magnetic stir bar
customThe crude reaction mixture
extractionextracted three times with an equivalent volume of ethyl acetate
dry with materialdried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-9736edbb7ff44f0e9be3b690cae21139
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645789B2

Reaction notes

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