1-Nitropropane → HCID 22638762, compound

HRID 1836664Notes

Reaction equation

HRID 1836664 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:7][CH:6]1[C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH:17]=O)=[CH:13][NH:14]2)=[CH:10][CH:9]=1)[CH3:3].P([O-])([O-])(O)=O.[NH4+].[NH4+].[N+:26](CCC)([O-])=O.[OH-].[Na+]>C(O)(=O)C.O>[CH3:1][N:2]([CH2:4][CH:5]1[CH2:7][CH:6]1[C:8]1[CH:16]=[C:15]2[C:11]([C:12]([C:17]#[N:26])=[CH:13][NH:14]2)=[CH:10][CH:9]=1)[CH3:3]

Participants

7

Reactant 4

HCID 79031-NitropropaneHCID 14798Sodium HydroxideHCID 24540Diammonium hydrogen phosphateHCID 22638733HCID 22638733, compound

Product 1

HCID 22638762HCID 22638762, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 5 mL of acetic acid were combined the crude 6-(2-dimethylaminomethyl-cyclo-propyl)-1H-indole-3-carbaldehyde, ammonium hydrogen phosphate (0.99 g, 7.50 mmol), and nitropropane (0.09 g, 1.03 mmol.). The mixture was stirred and heated to a gentle reflux for 16 h. Water was added after cooling reaction to room temperature, and the mixture was made basic by the addition of 1 N NaOH. The mixture was extracted with methylene chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give a brown oil. The oil was purified by flash chromatography (50% methanol/ethyl acetate) to give 6-(2-dimethylaminomethyl-cyclopropyl)-1H-indole-3-carbonitrile as an amber oil (93 mg, 38%). 1H NMR (CDCl3): δ7.58 (m, 2H), 6.99 (m, 2H), 5.75 (s, 1H), 2.46 (m, 1H), 2.33 (s, 7H), 1.89 (m, 1H), 1.20 (m, 1H), 0.98 (m, 1H), 0.86 (m, 1H); FIMS: 238.2 (M−H); LCMS: 72% AP.

Workup

  1. temperatureheated to
  2. temperaturea gentle reflux for 16 h
  3. temperatureafter cooling
  4. customreaction to room temperature
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a brown oil
  10. customThe oil was purified by flash chromatography (50% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-d02b7343ce594258b2a101be1c2707de
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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