Water → N-(6-chloro-9h-pyrido[3,4-b]indol-8-yl)-3-pyridinecarboxamide

HRID 1168734Notes

Reaction equation

HRID 1168734 reaction equation
N[N:2]1[C:14]2[CH:13]=[N:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5](Cl)=[CH:6][CH:7]=2.[ClH:16].C(Cl)C1C=C[CH:21]=[N:20]C=1.[OH2:25].[OH-].[Na+].[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[Cl:16][C:6]1[CH:7]=[C:8]2[C:3](=[C:4]([NH:20][C:21](=[O:25])[C:30]3[CH:31]=[CH:32][CH:33]=[N:28][CH:29]=3)[CH:5]=1)[NH:2][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1

Participants

6

Reactant 5

HCID 962Water2×HCID 1049PyridineHCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 221852799-Amino-7-chloro-beta-carboline

Product 1

HCID 9949093N-(6-chloro-9h-pyrido[3,4-b]indol-8-yl)-3-pyridinecarboxamide

Procedure

To a cold (3-5° C) solution of 9-amino-7-chloro-β-carboline (2.75 g, 12.7 mmol) in pyridine (150 ml) was added nicotinyl chloride hydrochloride (2.82 g, 15.8 mmol). The reaction was allowed to warm to RT and stirred for 20 h before diluting the reaction with water (100 ml) and 1M NaOH (25 ml). After stirring for 1 h at RT, the mixture was poured into water (200 ml). The mixture was allowed to stand for 1 h and the product was filtered to provide 3.80 g of the title compound after washing with water and drying under reduced pressure at RT.

Workup

  1. additionbefore diluting
  2. stirringAfter stirring for 1 h at RT
  3. waitto stand for 1 h
  4. filtrationthe product was filtered

Sources & evidence

ORD record
ord-05381e545b5c4a909b94c8059061fde8
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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