Potassium Hydroxide → HCID 71254050, compound

HRID 332108Notes

Reaction equation

HRID 332108 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]=[N:12][C:13]([CH:15]=O)=[CH:14][C:5]2=1.O.NN.[OH-].[K+]>C(O)CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]=[N:12][C:13]([CH3:15])=[CH:14][C:5]2=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86676795HCID 86676795, compound

Product 1

HCID 71254050HCID 71254050, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

Following a published procedure (Tetrahedron, 2002, 5251) 6-bromo-9H-pyrido[3,4-b]indole-3-carbaldehyde (40 mg, 0.145 mmol), hydrazine hydrate (51 mg, 1.02 mmol) and KOH (29 mg, 0.509 mmol) were combined in 0.5 mL of ethylene glycol and heated to 150° C. overnight. The reaction was cooled to room temperature. Ice chips were added and the mixture was stirred in an ice bath for 1 hour. White precipitate formed which was filtered and dried to afford the desired compound in 73% yield.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. additionIce chips were added
  3. customWhite precipitate formed which
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-7c269f1796804c9fae217744d0205685
Source dataset
uspto-grants-2014_11
Patent number
US08877797B2

Reaction notes

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