Phenylhydrazine → 2,5-dihydro-1H-pyrido[4,3-b]indol-1-one

HRID 1843993Notes

Reaction equation

HRID 1843993 reaction equation
O[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[C:9]1([NH:15]N)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[C:4]1(=[O:8])[C:3]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:15][C:2]=2[CH:7]=[CH:6][NH:5]1

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 546960044-Hydroxy-2(1H)-pyridinone

Product 1

HCID 121012772,5-dihydro-1H-pyrido[4,3-b]indol-1-oneYield 60.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 7583Diphenyl EtherSolvent

Procedure

4-Hydroxypyridin-2(1H)-one (3 g, 27 mmol) and phenylhydrazine (8.74 g, 81 mmol) in diphenyl ether (54 mL) were heated at 240° C. for 5 hours in a Dean Stark apparatus. The reaction mass was cooled to room temperature, diluted with benzene, stirred for 2 hours and filtered. The solid collected was dried under high vacuum and washed with ether to afford 3 g of the product (60% yield).

Workup

  1. filtrationfiltered
  2. customThe solid collected
  3. customwas dried under high vacuum
  4. washwashed with ether

Sources & evidence

ORD record
ord-9c087c494583407c9c3938c63e58cd90
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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