Sodium Hydroxide → HCID 19810693, compound

HRID 373582Notes

Reaction equation

HRID 373582 reaction equation
CN(C)[CH:3]=[CH:4][CH:5]=[O:6].P(Cl)(Cl)(Cl)=O.[CH3:13][C:14]1([CH3:33])[CH2:23][CH2:22][C:21]2[C:16]3=[C:17]([C:24]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:25][N:15]13)[CH:18]=[CH:19][CH:20]=2.[OH-].[Na+]>C(#N)C.O>[CH3:13][C:14]1([CH3:33])[CH2:23][CH2:22][C:21]2[C:16]3=[C:17]([C:24]([C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)=[C:25](/[CH:3]=[CH:4]/[CH:5]=[O:6])[N:15]13)[CH:18]=[CH:19][CH:20]=2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 791253-(Dimethylamino)-2-propenalHCID 19810698HCID 19810698, compound

Product 1

HCID 19810693HCID 19810693, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent3×

Procedure

A solution of 3-dimethylaminoacrylaldehyde (3.68 g) in dry acetonitrile (10 ml) was slowly added over a 30-minute period to a solution of phosphorus oxychloride (6.07 g) in dry acetonitrile (10 ml) with stirring at 0°-10° C. under nitrogen. A solution of 5,6-dihydro-4,4-dimethyl-1-(4-fluorophenyl)-4H-pyrrolo[3,2,1-ij]quinoline (3.70 g) in dry acetonitrile (9 ml) was slowly added to the reaction mixture at the same temperature. The reaction mixture was refluxed for 7 l hours under nitrogen, cooled to room temperature and slowly poured into a cold solution of sodium hydroxide (6.34 g) in water (130 ml) with stirring. The reaction mixture was extracted twice with toluene. The extracts were combined, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on a silica gel column eluting with a mixture of n-hexane and ethyl acetate (5:1, V/V). The fractions containing the object compound were collected and evaporated under reduced pressure. The residual oil was triturated with n-hexane to give yellow crystals of (E)-3-[5,6-dihydro-4,4-dimethyl-1-(4-fluorophenyl)-4H-pyrrolo[3,2,1-ij]quinolin-2-yl]acrylaldehyde (3.11 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 7 l hours under nitrogen
  2. stirringwith stirring
  3. extractionThe reaction mixture was extracted twice with toluene
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with a mixture of n-hexane and ethyl acetate (5:1, V/V)
  9. additionThe fractions containing the object compound
  10. customwere collected
  11. customevaporated under reduced pressure
  12. customThe residual oil was triturated with n-hexane

Sources & evidence

ORD record
ord-6cb13e35aad7443fbe6a64205b2609f7
Source dataset
uspto-grants-1992_11
Patent number
US05164400

Reaction notes

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