Hydrazine → 9-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carbohydrazide

HRID 992570Notes

Reaction equation

HRID 992570 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([C:18]([O:20]C)=O)=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[NH2:27][NH2:28]>CO>[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([C:18]([NH:27][NH2:28])=[O:20])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 9908122methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

Product 1

HCID 98214779-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carbohydrazideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 9-(2,5-dichlorobenzyl)-9H-β-carboline-3-carboxylate (4.8 g, 12.5 mmole), hydrazine (6 mL) and methanol (50 mL) was refluxed for 5 hours. The reaction mixture was cooled to room temperature, and the precipitate was collected by filtration. The solid was treated with methanol (50 mL) and the slurry stirred for 10 minutes, filtered, and dried, affording 4.6 grams (98%) of the title compound. 1H NMR (DMSO-d6) δ9.5 (s, 1H), 8.8 (s, 1H), 8.7 (s, 1H), 8.25 (d, 1H), 7.6-7.4 (m, 3H), 7.2-7.1 (m, 2H), 6.5 (s, 1H), 5.7 (s, 2H), 4.3 (s, 2H) MS (APCI; (M+H)+) m/z 385.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationthe precipitate was collected by filtration
  3. additionThe solid was treated with methanol (50 mL)
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-17570f1f4fc642e4afa5ccc163bf7e2d
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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