Hydrochloric Acid → HCID 178509533, compound

HRID 2064695Notes

Reaction equation

HRID 2064695 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[N:12]([O-])=O.[Na+].Cl.[OH2:17]>>[CH:7]([C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:8][N:12]=1)=[O:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27513Indole-5-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 178509533HCID 178509533, compound

Procedure

To a suspension of 5-cyanoindole (3.93 g) and sodium nitrite (19.07 g) in water was added 6M hydrochloric acid slowly until the pH was less than 2. The suspension was then stirred for 3 hours at ambient temperature. The mixture was then extracted with ethyl acetate, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo to give 3-formyl-1H-indazole-5-carbonitrile (4.5 g) as a pale brown solid. LC-MS (METHOD B): RT=2.47 minutes, 172.29 (M+H)+.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-20bcaf45412a4a6085cc5306b111e346
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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