Malonic Acid → HCID 3471468, compound

HRID 1586224Notes

Reaction equation

HRID 1586224 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[C:11]([OH:17])(=[O:16])[CH2:12]C(O)=O.C([O-])(=O)C.[NH4+:22]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]([NH2:22])[CH2:12][C:11]([OH:17])=[O:16])[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 90670m-FormylbenzonitrileHCID 517165Ammonium Acetate

Product 1

HCID 3471468HCID 3471468, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part A. The 3-cyano benzaldehyde (2.0 gm, 15.3 mmol), malonic acid (1.6 gm, 15.3 mmol) and ammonium acetate (2.37 gm, 30.75 mmol) were combined in 35 mLs ethanol under a nitrogen atmosphere. The reaction mixture was heated over night to become a thick slurry. The slurry was filtered and the solids were washed with additional ethanol. The 3-(cyano)-beta-(amino)benzene propanoic acid was isolated as a white powder 1.58 gm (55%) MS 191(M+H)+ 1 H NMR (DMSO-d6): 8.11(s, 1H), 7.96(d, 1H), 7.90(d, 1H), 7.46(t,1H), 5.7(s,4H), 4.66(m, 1H), 3.61(dd, 1H), 3.06(dd, 1H).

Workup

  1. temperatureThe reaction mixture was heated over night
  2. filtrationThe slurry was filtered
  3. washthe solids were washed with additional ethanol

Sources & evidence

ORD record
ord-f27b4713498947ad8d4f02a72c97d2e2
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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