4-Ethynylaniline → HCID 24770939, compound

HRID 1715304Notes

Reaction equation

HRID 1715304 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[C:7]([CH:9]=[N:10][OH:11])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[O-]Cl.[Na+].[C:23]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)#[CH:24]>C(Cl)Cl>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:8]=[C:7]([C:9]2[CH:24]=[C:23]([C:25]3[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=3)[O:11][N:10]=2)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 37600254-EthynylanilineHCID 23665760Sodium HypochloriteHCID 76599711HCID 76599711, compound

Product 1

HCID 24770939HCID 24770939, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-trifluoromethyl-biphenyl-4-carbaldehyde oxime (1 eq) in CH2Cl2 a 10% aqueous solution of NaOCl is added at 0° C. Thereafter a solution of 4-ethynylaniline (1.1 eq) is added and then the reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with CH2Cl2 and 3 times extracted with water. The combined organic layers are dried over Na2SO4, filtered and concentrated. Purification is achieved, after drying over Na2SO4, over silica gel using c-hexane/ethyl acetate 9/1→7/3 as mobile phase.

Workup

  1. extractionextracted with water
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification
  6. dry with materialafter drying over Na2SO4, over silica gel

Sources & evidence

ORD record
ord-b4035792e84741449b33beffa5e0c087
Source dataset
uspto-grants-2010_09
Patent number
US07799812B2

Reaction notes

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