1-Nitropropane → HCID 21102198, compound

HRID 2355953Notes

Reaction equation

HRID 2355953 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)NC=[C:5]2C=O.P([O-])([O-])(O)=O.[NH4+:18].[NH4+].[N+:20]([CH2:23][CH2:24][CH3:25])([O-])=O>C(O)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:8](=[C:4]([CH3:5])[CH:3]=1)[NH:20][CH:23]=[C:24]2[C:25]#[N:18]

Participants

5

Reactant 3

HCID 79031-NitropropaneHCID 24540Diammonium hydrogen phosphateHCID 701375-Bromoindole-3-carbaldehyde

Product 1

HCID 21102198HCID 21102198, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-bromo-indole-3-carboxaldehyde (0.7 g, 2.94 mmol), diammonium hydrogen phosphate (2.05 g, 15.5 mmol) in 1-nitropropane (9 mL) and acetic acid (3 mL) were heated at reflux for 16 h. After cooling to room temperature, the solvents were removed under reduced pressure and water added to the dark residue. After a short while, 5-bromo-1H-indole-3-carbonitrile precipitated rapidly, was filtered, washed severally with water and dried for several hours to afford 0.6 g (87%) of the desired nitrile. LC/MS: tR=1.71 min, 235.01 (MH)+.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 16 h
  3. customthe solvents were removed under reduced pressure and water
  4. additionadded to the dark residue
  5. customAfter a short while, 5-bromo-1H-indole-3-carbonitrile precipitated rapidly
  6. filtrationwas filtered
  7. washwashed severally with water
  8. customdried for several hours

Sources & evidence

ORD record
ord-e4e3ee4ef5664284ab963a5f6bf9977c
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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