Water → HCID 69209744, compound

HRID 32466Notes

Reaction equation

HRID 32466 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:13](#[N:17])[CH2:14][C:15]#[N:16].C(NCC)C.O>CN(C=O)C>[NH2:17][C:13]1[O:1][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[C:14]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 8021DiethylamineHCID 777862-Hydroxy-1-(4-methoxyphenyl)ethanone

Product 1

HCID 69209744HCID 69209744, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of 2-hydroxy-4′-methoxyacetophenone (379 mg, 2.28 mmol) in DMF (0.75 ml) was added malononitrile (166 mg, 2.51 mmol) followed by diethylamine (0.1 ml, 0.97 mmol). The mixture was stirred at room temperature for 2 hours, and then poured into large amount of cold water. The precipitate was filtrated, washed with water, and dried under reduced pressure to give the intermediate of Example 1(A) (424 mg, 87%) as a brown solid. 1H NMR (400 MHz, CDCl3) ppm 3.83 (s, 3H), 4.73 (brs, 2H), 6.93 (m, 2H), 6.94 (s, 1H), 7.49 (m, 2H). LC/MS: m/z 215 (M+1)+.

Workup

  1. filtrationThe precipitate was filtrated
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-55958ad6e27d49fa96299ad996a65ea7
Source dataset
uspto-grants-2008_09
Patent number
US07427623B2

Reaction notes

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