Acetic Acid → (Pyren-1-ylmethylene)malononitrile

HRID 2071220

Reaction equation

HRID 2071220 reaction equation
[C:1]1([CH:17]=O)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[C:19](#[N:23])[CH2:20][C:21]#[N:22].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C(O)C.ClC1C=CC=CC=1.O1CCCC1.C1C=CC=CC=1>[C:21]([C:20]([C:19]#[N:23])=[CH:17][C:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1)#[N:22]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 8010MalononitrileHCID 2328481-PyrenecarboxaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 290168(Pyren-1-ylmethylene)malononitrile

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 7964ChlorobenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

About 100 grams (0.434 moles) pyrene-1-carboxaldehyde, about 28.7 grams (0.434 moles) malononitrile, about 10.4 milliliters acetic acid, about 3.48 grams ammonium acetate and about 400 milliliters benzene are heated to boiling under reflux conditions for 30 minutes. The entire contents of the flask crystallized, forming a deep orange red product which is soluble in -tetrahydrofuran, moderately soluble in ethanol and very soluble in chlorobenzene. This product is recrystallized from a mixture of chlorobenzene and ethanol (30:70). Yield: 104.4 grams m. p 248°-250° C.

Workup

  1. customThe entire contents of the flask crystallized
  2. customforming a deep orange red product which
  3. customThis product is recrystallized from a mixture of chlorobenzene and ethanol (30:70)
  4. customp 248°-250° C.

Sources & evidence

ORD record
ord-594a1e39b8c946db91723e8bd20b0ad2
Source dataset
uspto-grants-1977_09
Patent number
US04046563

Linked notes

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