Malononitrile → HCID 18319895, compound

HRID 1699359Notes

Reaction equation

HRID 1699359 reaction equation
[OH-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Cl.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH:18]([NH2:20])[CH3:19])=[CH:13][CH:12]=1.C(#N)C(CC#N)O>O.C(O)C>[NH2:6][C:5]1[NH:20][C:18]([CH3:19])=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[C:4]=1[C:3]#[N:7]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 14798Sodium Hydroxide2×HCID 126265652-Amino-1-(4-methoxyphenyl)propan-1-one--hydrogen chloride (1/1)HCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 18319895HCID 18319895, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a refluxing solution (150 mL) of ethanol and water (7/3), NaOH (2.2 g, 55 mmol) and malononitrile (2.64 g, 40 mmol) were added. Then 4′-methoxy-2-aminopropiophenone hydrochloride (5.9 g, 27.2 mmol) was added in several portions. After the solution was refluxed for 30 minutes., additional malonitrile (1.3 g, 20 mmol) and NaOH (1.1 g, 27.5 mmol) were added. It was refluxed for additional 30 minutes and then poured into water (100 mL) which resulted in a precipitation. It was then filtered and washed with water until no color was washed out. The solid was then dried under vacuum at 50° C. overnight to give 2-amino-3-cyano-4-(4-methoxyphenyl)-5-methylpyrrole, (3.9 g, 63%). MS: 228 (MH+).

Workup

  1. temperatureAfter the solution was refluxed for 30 minutes
  2. temperatureIt was refluxed for additional 30 minutes
  3. customresulted in a precipitation
  4. filtrationIt was then filtered
  5. washwashed with water until no color
  6. washwas washed out
  7. customThe solid was then dried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-8a4db3ceffb44f70ab945eaee80cfba7
Source dataset
uspto-grants-2002_02
Patent number
US06346534B1

Reaction notes

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