Sodium Hydroxide → 1-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-ethylidene-amine

HRID 217299Notes

Reaction equation

HRID 217299 reaction equation
[Cl:1][C:2]1[C:3]([C:15]#[N:16])=[C:4]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:5]2=[C:6]([CH:14]=1)[CH2:7][O:8][CH2:9]3.[CH3:17][Al](C)C.C1(C)C=CC=CC=1.O.O.O.O.C([O-])(=O)C(C(C([O-])=O)O)O.[Na+].[K+].[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:15](=[NH:16])[CH3:17])=[C:4]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:5]2=[C:6]([CH:14]=1)[CH2:7][O:8][CH2:9]3

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2724148Sodium potassium tartrate tetrahydrateHCID 18425018Trimethylaluminium tolueneHCID 578987495-Chloro-1,3-dihydrobenzo[de]isochromene-6-carbonitrile

Product 1

HCID 578988321-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-ethylidene-amineYield 102.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

5-Chloro-1H,3H-benzo[de]isochromen-6-carbonitrile (20 g, 87.08 mmol) obtained in Step 5 of Example 71 was suspended in anhydrous toluene (100 mL) under nitrogen atmosphere, and 2 M trimethyl aluminum-toluene solution (218 mL, 435 mmol) was added at room temperature. The obtained solution was stirred while heating in a 105° C. oil bath for 12 hours. The reaction solution was cooled to room temperature, and then slowly poured into an aqueous solution of potassium sodium (+)-tartarate tetrahydrate (184 g). 2 N aqueous sodium hydroxide solution (250 mL) was additionally added, and after stirring for 30 minutes, this was extracted with ethyl acetate (500 mL). The separated organic layer was washed with water (300 mL) and brine, then dried over anhydrous sodium sulfate, filtered, concentrated, and thus, 1-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-ethylidene-amine (22 g) was obtained as an orange-colored oil like substance.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringafter stirring for 30 minutes
  3. extractionthis was extracted with ethyl acetate (500 mL)
  4. washThe separated organic layer was washed with water (300 mL) and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2385df99f89148f78991290de1d2952a
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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