Hydrochloric Acid → 2-Amino-5-(4-methoxyphenyl)-3-furancarbonitrile

HRID 32467Notes

Reaction equation

HRID 32467 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH2:9][CH:10]([C:13]#[N:14])[C:11]#[N:12])=[O:8])=[CH:5][CH:4]=1.Cl.O>C(O)(=O)C>[NH2:12][C:11]1[O:8][C:7]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=2)=[CH:9][C:10]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 153661992-(2-Oxo-2-(4-methoxyphenyl)ethyl)malononitrile

Product 1

HCID 241067882-Amino-5-(4-methoxyphenyl)-3-furancarbonitrileYield 57.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of α-((4-methoxybenzoyl)methyl)malononitrile (9.66 g, 45.1 mmol) in acetic acid (50 ml) was added conc. hydrogen chloride (11,3 ml). The mixture was stirred at room temperature for 2 hours, and then poured into water. The resultant precipitation was filtrated, washed with water and ethanol, and dried under reduced pressure to give the Intermediate of Example 2(A) (5.54 g, 56%) as a solid. 1H NMR (400 MHz, CDCl3) ppm 3.83 (s, 3H), 4.74 (brs, 2H), 6.39 (s, 1H), 6.90 (m, 2H), 7.42 (m, 2H).

Workup

  1. customThe resultant precipitation
  2. filtrationwas filtrated
  3. washwashed with water and ethanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-1996a01b8fb44706a2574631960b343b
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Reaction notes

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