Dimethylamine → 5-Cyanogramine

HRID 1463333Notes

Reaction equation

HRID 1463333 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].C=O.[CH3:14][NH:15][CH3:16].[CH:17](Cl)(Cl)Cl>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:14][N:15]([CH3:17])[CH3:16])#[N:2]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 6212ChloroformHCID 27513Indole-5-carbonitrile

Product 1

HCID 330335-CyanogramineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 14.0 g (98.5 mmol, 1.0 equiv.) of 5-cyanoindole in 35 mL of ethanol was added 8.7 mL (108 mmol, 1.1 equiv.) of 40% aqueous formaldehyde and 12.2 mL (108 mmol, 1.1 equiv) of 40% aqueous dimethylamine. The flask was fitted with a reflux condenser topped with a cold finger condenser at -78° C. The solution was heated to reflux for eight hours at which time TLC indicated absence of starting material. The solution was poured into 350 mL of chloroform and washed once with 50 mL of 10% aqueous sodium carbonate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated to yield 19.6 g (100%) of 5-cyano-3-(dimethylamino)methyl-1H-indole, pure by 1H NMR analysis.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. customtopped with a cold finger condenser at -78° C
  3. temperatureThe solution was heated
  4. temperatureto reflux for eight hours at which time TLC
  5. washwashed once with 50 mL of 10% aqueous sodium carbonate
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6e5e2b06f50946749f1acb867dc988ef
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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