ChemicalBook CAS DataBase List 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine

6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine synthesis

6synthesis methods

Product Name:6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine
CAS Number:352553-60-7
Molecular formula:C12H13ClN2
Molecular Weight:220.7

6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE

14192-67-7
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$12.00/1mg

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

352553-60-7
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Yield:352553-60-7 58%

Reaction Conditions:

with ammonium acetate;sodium cyanoborohydride in ethanol at 60;

Steps:

13 6-Chloro-2,3 ,4,9-tetrahydro- 1H-carb azol- 1-amine

6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (100 mg, 0.45 mmol), ammonium acetate (347 mg, 4.50 mmol) and sodium cyanoborohydride (141 mg, 2.25 mmol) weredissolved in ethanol (10 mL). The reaction mixture was stirred for overnight at 60 °C. After removal of solvent, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with 10% sodium hydroxide and brine, and it was dried over sodium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0-10% methanol/dichloromethane + 0.1% NH4OH) to give the product as awhite solid (57 mg, 58%);(DMSO-d6) 10.89 (bs, 1H), 7.34 (d, J= 2 Hz, 1H), 7.27 (d, J= 9 Hz,1H), 6.97 (dd, J= 9 Hz, J= 2 Hz, 1H), 6.68 (bs, 2H), 3.93-3.87 (m, 1H), 2.61-2.54 (m, 2H),2.03-1.90 (m, 2H), 1.73-1.66 (m, 1H), 1.55-1.46 (m, 1H); LC/IVIS RT = 2.55 (M-H: 219/221).

References:

WO2019/5841,2019,A1 Location in patent:Page/Page column 83; 84

14192-45-1 Synthesis