1-Nitropropane → HCID 22638762, compound

HRID 2416288Notes

Reaction equation

HRID 2416288 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-dimethylaminomethylcyclo-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): δ 7.58 (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-ba809935b6fe4bb6a9ce3bc51eef847d
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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