Propanedioyl dichloride → HCID 56603173, compound

HRID 1852491Notes

Reaction equation

HRID 1852491 reaction equation
[NH2:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17].[C:21](Cl)(=[O:26])[CH2:22][C:23](Cl)=[O:24]>O1CCCC1>[C:16]([C:15]1[CH:14]=[C:13]([N:12]2[C:23](=[O:24])[CH2:22][C:21](=[O:26])[NH:1][C:2]3[C:11]4[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=4[CH:5]=[CH:4][C:3]2=3)[CH:20]=[CH:19][CH:18]=1)#[N:17]

Participants

4

Reactant 2

HCID 74269Propanedioyl dichlorideHCID 86689305HCID 86689305, compound

Product 1

HCID 56603173HCID 56603173, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an anhydrous tetrahydrofuran (30 mL) solution of 3-(1-amino-5,6,7,8-tetrahydronaphthalen-2-ylamino)benzonitrile (747 mg, 2.84 mmol) was added an anhydrous tetrahydrofuran (5 mL) solution of malonyl chloride (276 μL, 2.84 mmol) under cooling in ice-bath. The mixture was stirred for 30 minutes under cooling in ice-bath, and for 2 hours at room temperature. To the mixture was added purified water. The mixture was extracted with ethyl acetate, washed with purified water, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=1/1) to give the titled compound as white powder (333 mg, yield 35%).

Workup

  1. temperatureunder cooling in ice-bath
  2. temperatureunder cooling in ice-bath
  3. waitfor 2 hours at room temperature
  4. additionTo the mixture was added
  5. custompurified water
  6. extractionThe mixture was extracted with ethyl acetate
  7. washwashed with purified water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed by evaporation under reduced pressure
  10. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-e9ed83fe3f94478c9e02ec87179bb85a
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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