Hydrazine hydrate (1:1) → (3S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carbohydrazide

HRID 1249101Notes

Reaction equation

HRID 1249101 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@@H:3]([C:14]([O:16]CC)=O)[NH:2]1.O.[NH2:20][NH2:21]>CN(C)C=O>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@@H:3]([C:14]([NH:20][NH2:21])=[O:16])[NH:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1079579ethyl (3S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

Product 1

HCID 7109654(3S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carbohydrazideYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (4.9 g), hydrazine hydrate (10 ml) and dimethylformamide (50 ml) is allowed to stand at room temperature overnight. The reaction mixture is is distilled under reduced pressure to remove the solvent. The residue is treated with ethyl acetate to give the title compound (3.40 g, 74%) as powder.

Workup

  1. distillationThe reaction mixture is is distilled under reduced pressure
  2. customto remove the solvent
  3. additionThe residue is treated with ethyl acetate

Sources & evidence

ORD record
ord-7bb566fabe9947ca831ad8d0c22c6d56
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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