Sodium Carbonate → 7-Bromo-2,3,4,9-tetrahydro-pyrido[3,4-b]indol-1-one

HRID 1515469Notes

Reaction equation

HRID 1515469 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8]N=C2CCCNC2=O)[CH:5]=[CH:6][CH:7]=1.[C:17](=[O:20])([O-])[O-].[Na+].[Na+]>C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:2]3[CH2:3][CH2:4][NH:8][C:17](=[O:20])[C:7]=3[NH:8]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 866498322,3-Piperidinedione 3-(3-bromophenyl)hydrazone

Product 1

HCID 581074207-Bromo-2,3,4,9-tetrahydro-pyrido[3,4-b]indol-1-oneYield 56%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2,3-piperidinedione 3-(3-bromophenyl) hydrazone (2.5 g, 22.3 mmol) in formic acid (40 mL) is refluxed for 1 h then cooled to room temperature. The reaction mixture is neutralized with sodium carbonate to basic condition. The resulting precipitate is filtered and collected. Recrystallization with ethanol provides 1.0 g (56%) of the title compound as a yellow solid.

Workup

  1. filtrationThe resulting precipitate is filtered
  2. customcollected
  3. customRecrystallization with ethanol

Sources & evidence

ORD record
ord-7a1613772b78445f94459d0e3928fbcb
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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