1-Nitropropane → HCID 21102198, compound

HRID 1177786Notes

Reaction equation

HRID 1177786 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-fcd4371ea46945f7835c6a79839c8434
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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