ChemicalBook CAS DataBase List 3-aminonorharman

3-aminonorharman synthesis

10synthesis methods

Product Name:3-aminonorharman
CAS Number:73834-77-2
Molecular formula:C11H9N3
Molecular Weight:183.21

9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLIC ACID HYDRAZIDE

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Yield:73834-77-2 78%

Reaction Conditions:

Stage #1: 9H-pyrido<3,4-b>indole-3-carboxylic acid hydrazidewith hydrogenchloride;NaNO₂ in lithium hydroxide monohydrate at 0;
Stage #2: with glacial acetic acid in lithium hydroxide monohydrate at 110; pH=8;

Steps:

1.6 (6) Synthesis of compounds 6a-6f:

Take 6a as an example, weigh 5a (10mmol) and place it in a 1L beaker, add water (200ml) and stir, then add concentrated hydrochloric acid (20ml), aqueous sodium nitrite (23mmol) to the solution. Stir for 10-30 min, keep the reaction temperature below 0 °C, and monitor the reaction by TLC. After the reaction was completed, the pH of the solution was adjusted to 8 with NaHCO3 and NaOH, and the solid was obtained by suction filtration (the solid was washed with a large amount of clean water, and could be directly used in the next step without drying). The product of the previous step (10 mmol) was added to a mixed solution of water (150 ml) and glacial acetic acid (150 ml), and refluxed at 110 °C for 2-4 h, (TLC monitoring reaction) after the reaction is completed, the solution is cooled, concentrated under reduced pressure to remove the solvent. The pH was adjusted to 8 with NaHCO3, the solution was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain compound 6a with a yield of 78%.

References:

CN114621225,2022,A Location in patent:Paragraph 0088; 0091; 0097; 0098