Acetic Acid → HCID 18997246, compound

HRID 374543Notes

Reaction equation

HRID 374543 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([CH3:20])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+]([O-])=O.Cl[C:22]1[CH:29]=[CH:28]C=C(Cl)C=1C=O.[C-]#[N:32].[K+].O.[C:35]([OH:38])(=O)[CH3:36]>>[C:35]([C:12]1[CH:13]=[C:14]2[C:15]([CH2:22][CH2:29][CH2:28]2)=[CH:16][C:11]=1[NH:10][CH:9]([C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])[C:20]#[N:32])(=[O:38])[CH3:36]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 67372,6-DichlorobenzaldehydeHCID 9032Potassium CyanideHCID 475457HCID 475457, compound

Product 1

HCID 18997246HCID 18997246, compoundYield 83.5%

Procedure

A solution of 3.5 g of intermediate (2) and 4.72 g of 2,6-dichlorobenzaldehyde in 100 ml of acetic acid was stirred for 2 hours at room temperature. 1.75 g of potassium cyanide was added and after stirring for 20 hours at room temperature, the reaction mixture was poured into water. The precipitated product was filtered off, washed with water and recrystallized from 2-propanol. The product was filtered off and dried, yielding 6 g (83.5%) of (±)-α-[(6-acetyl-2,3-dihydro-1H-inden-5-yl)amino]-2,6-dichlorobenzeneacetonitrile (interm. 17).

Workup

  1. filtrationThe precipitated product was filtered off
  2. washwashed with water
  3. customrecrystallized from 2-propanol
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-99834f1b652a4fdf9f3d6619571a7b64
Source dataset
uspto-grants-1996_01
Patent number
US05480912

Reaction notes

Loading…