Dimethylformamide → 6-Dipropylamino-1,5,6,7-tetrahydro-1-aza-s-indacen-3-carbaldehyde

HRID 1683891Notes

Reaction equation

HRID 1683891 reaction equation
[CH2:1]([N:4]([CH2:17][CH2:18][CH3:19])[CH:5]1[CH2:16][C:15]2[CH:14]=[C:13]3[C:9]([CH:10]=[CH:11][NH:12]3)=[CH:8][C:7]=2[CH2:6]1)[CH2:2][CH3:3].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:29]=[O:30]>>[CH2:17]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:16][C:15]2[CH:14]=[C:13]3[C:9]([C:10]([CH:29]=[O:30])=[CH:11][NH:12]3)=[CH:8][C:7]=2[CH2:6]1)[CH2:18][CH3:19]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 19041580Dipropyl-(1,5,6,7-tetrahydro-1-aza-s-indacen-6-yl)amine

Product 1

HCID 190415306-Dipropylamino-1,5,6,7-tetrahydro-1-aza-s-indacen-3-carbaldehydeYield 30%

Conditions

Temperature
50 °C

Procedure

A solution of dipropyl-(1,5,6,7-tetrahydro-1-aza-s-indacen-6-yl)amine (100 mg, 0.39 mmol) in dimethyl formamide (5 mL) was added to a solution of phosphorous oxychloride (200 μL, 329 mg, 2.14 mmol) in dimethyl formamide (5 mL) at -5° C. The mixture was heated at 50° C for 2 hours, poured on ice and treated with 5M sodium hydroxide and heated again for 20 minutes. After cooling, the mixture was extracted using dichloromethane. The combined organic extracts were dried (magnesium sulfate), filtered and evaporated to yield a residue of 70 mg, which was purified on silica using methanol as eluant, yielding 33 mg (30%) of the pure compound as an oil.:

Workup

  1. additionpoured on ice
  2. temperatureheated again for 20 minutes
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted
  5. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a residue of 70 mg, which
  9. customwas purified on silica

Sources & evidence

ORD record
ord-097c691fae3c4ba893c0abb70b7729e1
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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